Search for "palladium" in Full Text gives 676 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Beilstein J. Org. Chem. 2024, 20, 2784–2798, doi:10.3762/bjoc.20.234
Graphical Abstract
Figure 1: (A) Structures of tetrasubstituted 5,10,15,20-tetraphenylporphyrin (TPP, 1), dodecasubstituted 2,3,...
Scheme 1: Reaction scheme for the synthesis of OET-xBrPPs and subsequent Ni(II) metalation.
Figure 2: Substrates used for the investigations for the Suzuki–Miyaura coupling reactions.
Scheme 2: Scope of arm-extended dodecasubstituted porphyrins synthesized via modification of the meso-para-ph...
Scheme 3: Scope of arm-extended dodecasubstituted porphyrins synthesized via reaction at the meso-meta-phenyl...
Scheme 4: Attempts of arm-extension of dodecasubstituted porphyrins at the meso-ortho-phenyl position.
Scheme 5: Borylation and subsequent Suzuki–Miyaura coupling of porphyrin 13.
Figure 3: View of the molecular structure of compounds 26 (top left) and 27 (top right) with atomic displacem...
Figure 4: Left: packing diagram of 27 viewed normal to the c-axis showing the channels in the lattice with th...
Figure 5: Left: view of part 0 2 in the molecular structure of the α2β2-atropisomer, 11 in the crystal, hydro...
Figure 6: Schematic representation of porphyrin 37 showing a doubly intercalated structure.
Beilstein J. Org. Chem. 2024, 20, 2708–2719, doi:10.3762/bjoc.20.228
Graphical Abstract
Figure 1: Synthesis of uracil-based alkynes and aryl structures [51,62-65].
Figure 2: Structures of uracil derivatives A, B, and C.
Scheme 1: Strategy for the synthesis of the cyclised product 5. Conditions: i) Br2 (2 equiv), Ac2O (1.5 equiv...
Scheme 2: Synthesis and isolated yields of 1,3-dimethyl-5-aryl-6-[2-(aryl)ethynyl]uracils 4a–i. Reaction cond...
Scheme 3: Scope and isolated yields of the synthesis of 5. Reaction conditions: 4 (1 equiv), p-TsOH·H2O (20 e...
Scheme 4: Proposed reaction mechanism of the cyclisation with N,N-dimethylanilino functional groups.
Figure 3: UV–vis absorption (left) and emission (right, λex = 400 nm) spectra of 5a, 5d, 5f, 5g, 5h, and 5i i...
Beilstein J. Org. Chem. 2024, 20, 2704–2707, doi:10.3762/bjoc.20.227
Beilstein J. Org. Chem. 2024, 20, 2691–2703, doi:10.3762/bjoc.20.226
Graphical Abstract
Scheme 1: Synthesis of monofluoroalkenes using fluorine-containing building blocks.
Beilstein J. Org. Chem. 2024, 20, 2592–2598, doi:10.3762/bjoc.20.218
Graphical Abstract
Figure 1: Aminoquinazolines and our new target molecules.
Scheme 1: Synthesis of the desired targets 4.
Figure 2: Target molecules 4 prepared with the yields for the last step.
Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214
Graphical Abstract
Figure 1: Classification of LSF reactions in this review.
Scheme 1: C(sp2)–H trifluoromethylation of heteroarenes.
Scheme 2: C(sp2)–H and C(sp3)–H alkylation of complex molecules.
Scheme 3: Electrochemical oxidation-induced intermolecular aromatic C–H sulfonamidation.
Scheme 4: Bioconjugation of tyrosine with (a) phenothiazine and (b) urazole derivatives.
Scheme 5: Electrochemical iodoamination of indoles using unactivated amines.
Scheme 6: Allylic C(sp3)–H aminations with sulfonamides.
Scheme 7: Electrochemical benzylic oxidation of C–H bonds.
Scheme 8: Site-selective electrooxidation of methylarenes to aromatic acetals.
Scheme 9: Electrochemical activation of C–H by electron-deficient W2C nanocrystals.
Scheme 10: α-Acyloxy sulfide preparation via C–H/OH cross-dehydrogenative coupling.
Scheme 11: Aromatic C–H-bond thiolation.
Scheme 12: C(sp2)–H functionalization for the installation of sulfonamide groups.
Scheme 13: Preparation of (hetero)aryl chlorides and vinyl chloride with 1,2-dichloroethane. aCu(OAc)2 (0.05 e...
Scheme 14: Electrochemical dual-oxidation enables access to α-chlorosulfoxides.
Scheme 15: Regio- and chemoselective formyloxylation–bromination/chlorination/trifluoromethylation of alkenes.
Scheme 16: Aziridine formation by coupling amines and alkenes.
Scheme 17: Formation of iminosulfide ethers via difunctionalization of an isocyanide.
Scheme 18: Synthesis of 1,3-difunctionalized molecules via C–C-bond cleavage of arylcyclopropane.
Scheme 19: Electrooxidative amino- and oxyselenation of alkenes. VBImBr = 1-butyl-3-vinylimidazolium bromide.
Scheme 20: Electrooxidative dehydrogenative [4 + 2] annulation of indole derivatives.
Scheme 21: Electrochemical cyclization combined with alkoxylation of triticonazole.
Scheme 22: Electrochemically tuned oxidative [4 + 2] annulation of olefins with hydroxamic acids.
Scheme 23: Electrosynthesis of indole derivatives via cyclization of 2-ethynylanilines.
Scheme 24: Allylic C–H oxidation of mono-, di-, and sesquiterpenes.
Scheme 25: Oxidation of unactivated C–H bonds.
Scheme 26: Fluorination of C(sp3)–H bonds. rAP = rapid alternating polarity.
Scheme 27: C(sp3)–H α-cyanation of secondary piperidines.
Scheme 28: Selective electrochemical hydrolysis of hydrosilanes to silanols.
Scheme 29: Organocatalytic electrochemical amination of benzylic C–H bonds.
Scheme 30: Iodide ion-initiated anodic oxidation reactions.
Scheme 31: Mn(III/IV) electro-catalyzed C(sp3)–H azidation.
Scheme 32: Tailored cobalt–salen complexes enable electrocatalytic intramolecular allylic C–H functionalizatio...
Scheme 33: Cobalt–salen complexes-induced electrochemical (cyclo)additions.
Scheme 34: Electrochemical 1,2-diarylation of alkenes enabled by direct dual C–H functionalization of electron...
Scheme 35: Cobalt-electrocatalyzed atroposelective C–H annulation.
Scheme 36: Nickel-electrocatalyzed C(sp2)–H alkoxylation with secondary alcohols.
Scheme 37: Nickel-catalyzed electrochemical enantioselective amination.
Scheme 38: Ruthenium-electrocatalyzed C(sp2)–H mono- and diacetoxylation.
Scheme 39: Rhodium(III)-catalyzed aryl-C–H phosphorylation enabled by anodic oxidation-induced reductive elimi...
Scheme 40: Asymmetric Lewis-acid catalysis for the synthesis of non-racemic 1,4-dicarbonyl compounds.
Scheme 41: Electrochemical enantioselective C(sp3)–H alkenylation.
Scheme 42: Palladium-catalyzed electrochemical dehydrogenative cross-coupling.
Scheme 43: Ir-electrocatalyzed vinylic C(sp2)–H activation for the annulation between acrylic acids and alkyne...
Scheme 44: Electrochemical gold-catalyzed C(sp3)–C(sp) coupling of alkynes and arylhydrazines.
Scheme 45: Photoelectrochemical alkylation of C–H heteroarenes using organotrifluoroborates.
Scheme 46: Mn-catalyzed photoelectro C(sp3)–H azidation.
Scheme 47: Photoelectrochemical undirected C–H trifluoromethylations of (Het)arenes.
Scheme 48: Photoelectrochemical dehydrogenative cross-coupling of heteroarenes with aliphatic C–H bonds.
Scheme 49: C–H amination via photoelectrochemical Ritter-type reaction.
Scheme 50: Photoelectrochemical multiple oxygenation of C–H bonds.
Scheme 51: Accelerated C(sp3)–H heteroarylations by the f-EPC system.
Scheme 52: Photoelectrochemical cross-coupling of amines.
Scheme 53: Birch electroreduction of arenes. GSW = galvanized steel wire.
Scheme 54: Electroreductive deuterations.
Scheme 55: Chemoselective electrosynthesis using rapid alternating polarity.
Scheme 56: Electroreductive olefin–ketone coupling.
Scheme 57: Electroreductive approach to radical silylation.
Scheme 58: Electrochemical borylation of alkyl halides. CC = carbon close.
Scheme 59: Radical fluoroalkylation of alkenes.
Scheme 60: Electrochemical defluorinative hydrogenation/carboxylation.
Scheme 61: Electrochemical decarboxylative olefination.
Scheme 62: Electrochemical decarboxylative Nozaki–Hiyama–Kishi coupling.
Scheme 63: Nickel-catalyzed electrochemical reductive relay cross-coupling.
Scheme 64: Electrochemical chemo- and regioselective difunctionalization of 1,3-enynes.
Scheme 65: Electrocatalytic doubly decarboxylative crosscoupling.
Scheme 66: Electrocatalytic decarboxylative crosscoupling with aryl halides.
Scheme 67: Nickel-catalyzed electrochemical reductive coupling of halides.
Scheme 68: Nickel-electrocatalyzed enantioselective carboxylation with CO2.
Scheme 69: Reductive electrophotocatalysis for borylation.
Scheme 70: Electromediated photoredox catalysis for selective C(sp3)–O cleavages of phosphinated alcohols to c...
Scheme 71: Stereoselective electro-2-deoxyglycosylation from glycals. MFE = methyl nonafluorobutyl ether.
Scheme 72: Electrochemical peptide modifications.
Scheme 73: Electrochemical α-deuteration of amides.
Scheme 74: Electrochemical synthesis of gem-diselenides.
Scheme 75: Site-selective electrochemical aromatic C–H amination.
Scheme 76: Electrochemical coupling of heteroarenes with heteroaryl phosphonium salts.
Scheme 77: Redox-neutral strategy for the dehydroxyarylation reaction.
Scheme 78: Nickel-catalyzed electrochemical C(sp3)–C(sp2) cross-coupling of benzyl trifluoroborate and halides....
Scheme 79: Paired electrocatalysis for C(sp3)–C(sp2) coupling.
Scheme 80: Redox-neutral strategy for amination of aryl bromides.
Scheme 81: Redox-neutral cross-coupling of aryl halides with weak N-nucleophiles. aProtocol with (+) RVC | RVC...
Scheme 82: Nickel-catalyzed N-arylation of NH-sulfoximines with aryl halides.
Scheme 83: Esterification of carboxylic acids with aryl halides.
Scheme 84: Electrochemically promoted nickel-catalyzed carbon–sulfur-bond formation. GFE = graphite felt elect...
Scheme 85: Electrochemical deoxygenative thiolation by Ni-catalysis. GFE = graphite felt electrode; NFE = nick...
Scheme 86: Electrochemical coupling of peptides with aryl halides.
Scheme 87: Paired electrolysis for the phosphorylation of aryl halides. GFE = graphite felt electrode, FNE = f...
Scheme 88: Redox-neutral alkoxyhalogenation of alkenes.
Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187
Graphical Abstract
Figure 1: Examples of compounds covered in this review categorized in six sub-classes (see text).
Figure 2: Examples of compounds not covered in this review.
Figure 3: Wrongly assigned and thus obsolete structures (details will be discussed in the respective chapters...
Figure 4: Alternariol with the correct IUPAC numbering and an occasionally used numbering based on the biphen...
Figure 5: Alternariol O-methyl ethers.
Figure 6: Alternariol O-glycosides.
Figure 7: Alternariol O-acetates and O-sulfates.
Figure 8: 2-Hydroxy- and 4-hydroxy-substituted alternariol and its O-methyl ethers.
Figure 9: Chloro- and amino-substituted alternariol and its O-methyl ethers.
Figure 10: Presumed alternariol derivatives with non-canonical substitution pattern.
Figure 11: Alternariol derivatives with the 1-methyl group hydroxylated.
Figure 12: Verrulactones: pseudo-dimeric derivatives of altertenuol and related compounds.
Figure 13: Biaryls formed by reductive lactone opening and/or by decarboxylation.
Figure 14: Altenuene and its diastereomers.
Figure 15: 9-O-Demethylated altenuene diastereomers.
Figure 16: Acetylated and methylated altenuene diastereomers.
Figure 17: Altenuene diastereomers modified with lactic acid, pyruvic acid, or acetone.
Figure 18: Neoaltenuene and related compounds.
Figure 19: Dehydroaltenusin and its derivatives.
Scheme 1: Equilibrium of dehydroaltenusin in polar solvents [278].
Figure 20: Further quinoid derivatives.
Figure 21: Dehydroaltenuenes.
Figure 22: Complex aggregates containing dehydroaltenuene substructures and related compounds.
Figure 23: Dihydroaltenuenes.
Figure 24: Altenuic acids and related compounds.
Figure 25: Cyclopentane- and cyclopentene-fused derivatives.
Figure 26: Cyclopentenone-fused derivatives.
Figure 27: Spiro-fused derivatives and a related ring-opened derivative.
Figure 28: Lactones-fused and lactone-substituted derivatives.
Scheme 2: Biosynthesis of alternariol [324].
Scheme 3: Biosynthesis of alternariol and its immediate successors with the genes involved in the respective ...
Scheme 4: Presumed formation of altenuene and its diastereomers and of botrallin.
Scheme 5: Presumed formation of altenuic acids and related compounds.
Scheme 6: A selection of plausible biosynthetic paths to cyclopenta-fused metabolites. (No stereochemistry is...
Scheme 7: Biomimetic synthesis of alternariol (1) by Harris and Hay [66].
Scheme 8: Total synthesis of alternariol (1) by Subba Rao et al. using a Diels–Alder approach [34].
Scheme 9: Total synthesis of alternariol (1) using a Suzuki strategy by Koch and Podlech [62], improved by Kim et...
Scheme 10: Total synthesis of alternariol (1) using an intramolecular biaryl coupling by Abe et al. [63].
Scheme 11: Total synthesis of altenuene (54) and isoaltenuene (55) by Podlech et al. [249].
Scheme 12: Total synthesis of neoaltenuene (69) by Podlech et al. [35].
Scheme 13: Total synthesis of TMC-264 (79) by Tatsuta et al. [185].
Scheme 14: Total synthesis of cephalosol (99) by Koert et al. [304].
Beilstein J. Org. Chem. 2024, 20, 2114–2128, doi:10.3762/bjoc.20.182
Graphical Abstract
Figure 1: Resonance structures and reactivity of carbon monoxide.
Figure 2: Resonance structures and reactivity of isocyanides.
Scheme 1: Possible three pathways of the E• formation for imidoylation.
Scheme 2: Radical addition of thiols to isocyanides.
Scheme 3: Selective thioselenation and catalytic dithiolation of isocyanides.
Scheme 4: Synthesis of carbacephem framework.
Scheme 5: Sequential addition of (PhSe)2 to ethyl propiolate and isocyanide.
Scheme 6: Isocyanide insertion reaction into carbon-tellurium bonds.
Scheme 7: Radical addition to isocyanides with disubstituted phosphines.
Scheme 8: Radical addition to phenyl isocyanides with diphosphines.
Scheme 9: Radical reaction of tin hydride and hydrosilane toward isocyanide.
Scheme 10: Isocyanide insertion into boron compounds.
Scheme 11: Isocyanide insertion into cyclic compounds containing boron units.
Scheme 12: Photoinduced hydrodefunctionalization of isocyanides.
Scheme 13: Tin hydride-mediated indole synthesis and cross-coupling.
Scheme 14: 2-Thioethanol-mediated radical cyclization of alkenyl isocyanide.
Scheme 15: Thiol-mediated radical cyclization of o-alkenylaryl isocyanide.
Scheme 16: (PhTe)2-assisted dithiolative cyclization of o-alkenylaryl isocyanide.
Scheme 17: Trapping imidoyl radicals with heteroatom moieties.
Scheme 18: Trapping imidoyl radicals with isocyano group.
Scheme 19: Quinoline synthesis via aza-Bergman cyclization.
Scheme 20: Phenanthridine synthesis via radical cyclization of 2-isocyanobiaryls.
Scheme 21: Phenanthridine synthesis by radical reactions with AIBN, DBP and TTMSS.
Scheme 22: Phenanthridine synthesis by oxidative cyclization of 2-isocyanobiaryls.
Scheme 23: Phenanthridine synthesis using a photoredox system.
Scheme 24: Phenanthridine synthesis induced by phosphorus-centered radicals.
Scheme 25: Phenanthridine synthesis induced by sulfur-centered radicals.
Scheme 26: Phenanthridine synthesis induced by boron-centered radicals.
Scheme 27: Phenanthridine synthesis by oxidative cyclization of 2-aminobiaryls.
Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178
Graphical Abstract
Scheme 1: Consecutive three-component synthesis of pyrazoles 1 via in situ-formed 1,3-diketones 2 [44].
Scheme 2: Consecutive three-component synthesis of 4-ethoxycarbonylpyrazoles 5 via SmCl3-catalyzed acylation ...
Scheme 3: Consecutive four-component synthesis of 1-(thiazol-2-yl)pyrazole-3-carboxylates 8 [51].
Scheme 4: Three-component synthesis of thiazolylpyrazoles 17 via in situ formation of acetoacetylcoumarins 18 ...
Scheme 5: Consecutive pseudo-four-component and four-component synthesis of pyrazoles 21 from sodium acetylac...
Scheme 6: Consecutive three-component synthesis of 1-substituted pyrazoles 24 from boronic acids, di(Boc)diim...
Scheme 7: Consecutive three-component synthesis of N-arylpyrazoles 25 via in situ formation of aryl-di(Boc)hy...
Scheme 8: Consecutive three-component synthesis of 1,3,4-substituted pyrazoles 27 and 28 from methylhydrazine...
Scheme 9: Consecutive three-component synthesis of 4-allylpyrazoles 32 via oxidative allylation of 1,3-dicarb...
Scheme 10: Pseudo-five-component synthesis of tris(pyrazolyl)methanes 35 [61].
Scheme 11: Pseudo-three-component synthesis of 5-(indol-3-yl)pyrazoles 39 from 1,3,5-triketones 38 [64].
Scheme 12: Three-component synthesis of thiazolylpyrazoles 43 [65].
Scheme 13: Three-component synthesis of triazolo[3,4-b]-1,3,4-thiadiazin-3-yl substituted 5-aminopyrazoles 47 [67]....
Scheme 14: Consecutive three-component synthesis of 5-aminopyrazoles 49 via formation of β-oxothioamides 50 [68].
Scheme 15: Synthesis of 3,4-biarylpyrazoles 52 from aryl halides, α-bromocinnamaldehyde, and tosylhydrazine vi...
Scheme 16: Consecutive three-component synthesis of 3,4-substituted pyrazoles 57 from iodochromones 55 by Suzu...
Scheme 17: Pseudo-four-component synthesis of pyrazolyl-2-pyrazolines 59 by ring opening/ring closing cyclocon...
Scheme 18: Consecutive three-component synthesis of pyrazoles 61 [77].
Scheme 19: Three-component synthesis of pyrazoles 62 from malononitrile, aldehydes, and hydrazines [78-90].
Scheme 20: Four-component synthesis of pyrano[2,3-c]pyrazoles 63 [91].
Scheme 21: Three-component synthesis of persubstituted pyrazoles 65 from aldehydes, β-ketoesters, and hydrazin...
Scheme 22: Three-component synthesis of pyrazol-4-carbodithioates 67 [100].
Scheme 23: Regioselective three-component synthesis of persubstituted pyrazoles 68 catalyzed by ionic liquid [...
Scheme 24: Consecutive three-component synthesis of 4-halopyrazoles 69 and anellated pyrazoles 70 [102].
Scheme 25: Three-component synthesis of 2,2,2-trifluoroethyl pyrazole-5-carboxylates 72 [103].
Scheme 26: Synthesis of pyrazoles 75 in a one-pot process via carbonylative Heck coupling and subsequent cycli...
Scheme 27: Copper-catalyzed three-component synthesis of 1,3-substituted pyrazoles 76 [105].
Scheme 28: Pseudo-three-component synthesis of bis(pyrazolyl)methanes 78 by ring opening-ring closing cyclocon...
Scheme 29: Three-component synthesis of 1,4,5-substituted pyrazoles 80 [107].
Scheme 30: Consecutive three-component synthesis of 3,5-bis(fluoroalkyl)pyrazoles 83 [111].
Scheme 31: Consecutive three-component synthesis of difluoromethanesulfonyl-functionalized pyrazole 88 [114].
Scheme 32: Consecutive three-component synthesis of perfluoroalkyl-substituted fluoropyrazoles 91 [115].
Scheme 33: Regioselective consecutive three-component synthesis of 1,3,5-substituted pyrazoles 93 [116].
Scheme 34: Three-component synthesis of pyrazoles 96 mediated by trimethyl phosphite [117].
Scheme 35: One-pot synthesis of pyrazoles 99 via Liebeskind–Srogl cross-coupling/cyclocondensation [118].
Scheme 36: Synthesis of 1,3,5-substituted pyrazoles 101 via domino condensation/Suzuki–Miyaura cross-coupling ...
Scheme 37: Consecutive three-component synthesis of 1,3,5-trisubstituted pyrazoles 102 and 103 by Sonogashira ...
Scheme 38: Polymer analogous consecutive three-component synthesis of pyrazole-based polymers 107 [132].
Scheme 39: Synthesis of 1,3,5-substituted pyrazoles 108 by sequentially Pd-catalyzed Kumada–Sonogashira cycloc...
Scheme 40: Consecutive four-step one-pot synthesis of 1,3,4,5-substituted pyrazoles 110 [137].
Scheme 41: Four-component synthesis of pyrazoles 113, 115, and 117 via Sonogashira coupling and subsequent Suz...
Scheme 42: Consecutive four- or five-component synthesis for the preparation of 4-pyrazoly-1,2,3-triazoles 119...
Scheme 43: Four-component synthesis of pyrazoles 121 via alkynone formation by carbonylative Pd-catalyzed coup...
Scheme 44: Preparation of 3-azulenyl pyrazoles 124 by glyoxylation, decarbonylative Sonogashira coupling, and ...
Scheme 45: Four-component synthesis of a 3-indoloylpyrazole 128 [147].
Scheme 46: Two-step synthesis of 5-acylpyrazoles 132 via glyoxylation-Stephen–Castro sequence and subsequent c...
Scheme 47: Copper on iron mediated consecutive three-component synthesis of 3,5-substituted pyrazoles 136 [150].
Scheme 48: Consecutive three-component synthesis of 3-substituted pyrazoles 141 by Sonogashira coupling and su...
Scheme 49: Consecutive three-component synthesis of pyrazoles 143 initiated by Cu(I)-catalyzed carboxylation o...
Scheme 50: Consecutive three-component synthesis of benzamide-substituted pyrazoles 146 starting from N-phthal...
Scheme 51: Consecutive three-component synthesis of 1,3,5-substituted pyrazoles 148 [156].
Scheme 52: Three-component synthesis of 4-ninhydrin-substituted pyrazoles 151 [158].
Scheme 53: Consecutive four-component synthesis of 4-(oxoindol)-1-phenylpyrazole-3-carboxylates 155 [159].
Scheme 54: Three-component synthesis of pyrazoles 160 [160].
Scheme 55: Consecutive three-component synthesis of pyrazoles 165 [162].
Scheme 56: Consecutive three-component synthesis of 3,5-disubstituted and 3-substituted pyrazoles 168 and 169 ...
Scheme 57: Three-component synthesis of 3,4,5-substituted pyrazoles 171 via 1,3-dipolar cycloaddition of vinyl...
Scheme 58: Three-component synthesis of pyrazoles 173 and 174 from aldehydes, tosylhydrazine, and vinylidene c...
Scheme 59: Three-component synthesis of pyrazoles 175 from glyoxyl hydrates, tosylhydrazine, and electron-defi...
Scheme 60: Pseudo-four-component synthesis of pyrazoles 177 from glyoxyl hydrates, tosylhydrazine, and aldehyd...
Scheme 61: Consecutive three-component synthesis of pyrazoles 179 via Knoevenagel-cycloaddition sequence [179].
Scheme 62: Three-component synthesis of 5-dimethylphosphonate substituted pyrazoles 182 from aldehydes, the Be...
Scheme 63: Consecutive three-component synthesis of 5-(dimethyl phosphonate)-substituted pyrazoles 185 from al...
Scheme 64: Three-component synthesis of 5-(dimethyl phosphonate)-substituted pyrazoles 187 from aldehydes, the...
Scheme 65: Three-component synthesis of 5-diethylphosphonate/5-phenylsulfonyl substituted pyrazoles 189 from a...
Scheme 66: Pseudo-three-component synthesis of 3-(dimethyl phosphonate)-substituted pyrazoles 190 [185].
Scheme 67: Three-component synthesis of 3-trifluoromethylpyrazoles 193 [186].
Scheme 68: Consecutive three-component synthesis of 5-stannyl-substituted 4-fluoropyrazole 197 [191,192].
Scheme 69: Pseudo-three-component synthesis of 3,5-diacyl-4-arylpyrazoles 199 [195].
Scheme 70: Three-component synthesis of pyrazoles 204 via nitrilimines [196].
Scheme 71: Three-component synthesis of 1,3,5-substituted pyrazoles 206 via formation of nitrilimines and sali...
Scheme 72: Pseudo four-component synthesis of pyrazoles 209 from acetylene dicarboxylates 147, hydrazonyl chlo...
Scheme 73: Consecutive three-component synthesis of pyrazoles 213 via syndnones 214 [200].
Scheme 74: Consecutive three-component synthesis of pyrazoles 216 via in situ-formed diazomethinimines 217 [201].
Scheme 75: Consecutive three-component synthesis of 3-methylthiopyrazoles 219 from aldehydes, hydrazine, and 1...
Scheme 76: Three-component synthesis of 1,3,5-substituted pyrazoles 220 from aldehydes, hydrazines, and termin...
Scheme 77: Three-component synthesis of 1,3,4,5-substituted pyrazoles 222 from aldehydes, hydrazines, and DMAD ...
Scheme 78: Pseudo three-component synthesis of pyrazoles 224 from sulfonyl hydrazone and benzyl acrylate under...
Scheme 79: Titanium-catalyzed consecutive four-component synthesis of pyrazoles 225 via enamino imines 226 [211]. a...
Scheme 80: Titanium-catalyzed three-component synthesis of pyrazoles 227 via enhydrazino imine complex interme...
Scheme 81: Pseudo-three-component synthesis of pyrazoles 229 via Glaser coupling of terminal alkynes and photo...
Scheme 82: Copper(II)acetate-mediated three-component synthesis of pyrazoles 232 [216].
Scheme 83: Copper-catalyzed three-component synthesis of 1,3,4-substituted pyrazole 234 from oxime acetates, a...
Scheme 84: Three-component synthesis of 3-trifluoroethylpyrazoles 239 [218].
Scheme 85: Pseudo-three-component synthesis of 1,4-bisulfonyl-substituted pyrazoles 242 [219].
Scheme 86: Three-component synthesis of 4-hydroxypyrazole 246 [221].
Beilstein J. Org. Chem. 2024, 20, 1922–1932, doi:10.3762/bjoc.20.168
Graphical Abstract
Scheme 1: Known and improved synthetic strategies to access α-(hetero)aryl-amino acids.
Scheme 2: Reformatsky reagent production.
Scheme 3: Scope of ethyl heteroarylacetates. Isolated yields are given. *Dark reactions were carried out for ...
Scheme 4: Telescoped flow synthesis of heteroarylacetates.
Scheme 5: Potential routes for the preparation of oximes.
Scheme 6: Oxime group insertion step.
Scheme 7: Amino ester production: general scheme, scope and gram scale experiment. The numbers in brackets re...
Scheme 8: Reactions scheme and results for the on-DNA experiments. The reported values represent the normaliz...
Beilstein J. Org. Chem. 2024, 20, 1914–1921, doi:10.3762/bjoc.20.167
Graphical Abstract
Figure 1: Selected natural products, pharmaceuticals, and biologically active compounds having an isoquinolin...
Scheme 1: Chemoselective and PISA-mediated, solvent-controlled synthesis of different isoquinolinone derivati...
Scheme 2: Substrate scope for the synthesis of 4-substituted isoquinolinones 2. Reaction conditions: 1 (0.3 m...
Scheme 3: Optimal reaction conditions for the synthesis of 3-substituted isoquinolinone 3a.
Scheme 4: Substrate scope for the synthesis of 3-substituted isoquinolinones 3. Reaction conditions: 1 (0.3 m...
Scheme 5: Control experiment to test for radical intermediates.
Scheme 6: Proposed mechanism for the reaction between 1a and PISA in anhydrous acetonitrile.
Scheme 7: Two other resonance structures of the intermediate 1CC.
Scheme 8: Proposed mechanism for the reaction between 1a and PISA in wet HFIP.
Beilstein J. Org. Chem. 2024, 20, 1900–1905, doi:10.3762/bjoc.20.165
Graphical Abstract
Scheme 1: Radical and ionic intramolecular cyclizations.
Scheme 2: Electrochemical and photochemical aza-Wacker cyclizations.
Scheme 3: Scope of electrochemical aza-Wacker cyclization. Reaction conditions: the alkene (0.20 mmol), Bu4NO...
Scheme 4: Mechanistic studies of aza-Wacker cyclization. A: Electrochemical (Bu4NOTf in CH3CN/1,2-DCE), B: no...
Figure 1: Cyclic voltammograms for aryl sulfonamides.
Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162
Graphical Abstract
Scheme 1: Mechanism of the GBB reaction.
Scheme 2: Comparison of the performance of Sc(OTf)3 with some RE(OTf)3 in a model GBB reaction. Conditions: a...
Scheme 3: Comparison of the performance of various Brønsted acid catalysts in the synthesis of GBB adduct 6. ...
Scheme 4: Synthesis of Brønsted acidic ionic liquid catalyst 7. Conditions: a) neat, 60 °C, 24 h; b) TfOH, DC...
Scheme 5: Aryliodonium derivatives as organic catalysts in the GBB reaction. In the box the proposed binding ...
Scheme 6: DNA-encoded GBB reaction in micelles made of amphiphilic polymer 13. Conditions: a) 13 (50 equiv), ...
Scheme 7: GBB reaction catalyzed by cyclodextrin derivative 14. Conditions: a) 14 (1 mol %), water, 100 °C, 4...
Scheme 8: Proposed mode of activation of CALB. a) activation of the substrates; b) activation of the imine; c...
Scheme 9: One-pot GBB reaction–Suzuki coupling with a bifunctional hybrid biocatalyst. Conditions: a) Pd(0)-C...
Scheme 10: GBB reaction employing 5-HMF (23) as carbonyl component. Conditions: a) TFA (20 mol %), EtOH, 60 °C...
Scheme 11: GBB reaction with β-C-glucopyranosyl aldehyde 26. Conditions: a) InCl3 (20 mol %), MeOH, 70 °C, 2–3...
Scheme 12: GBB reaction with diacetylated 5-formyldeoxyuridine 29, followed by deacetylation of GBB adduct 30....
Scheme 13: GBB reaction with glycal aldehydes 32. Conditions: a) HFIP, 25 °C, 2–4 h.
Scheme 14: Vilsmeier–Haack formylation of 6-β-acetoxyvouacapane (34) and subsequent GBB reaction. Conditions: ...
Scheme 15: GBB reaction of 4-formlyl-PCP 37. Conditions: a) HOAc or HClO4, MeOH/DCM (2:3), rt, 3 d.
Scheme 16: GBB reaction with HexT-aldehyde 39. Conditions: a) 39 (20 nmol) and amidine (20 μmol), MeOH, rt, 6 ...
Scheme 17: GBB reaction of 2,4-diaminopirimidine 41. Conditions: a) Sc(OTf)3 (20 mol %), MeCN, 120 °C (MW), 1 ...
Scheme 18: Synthesis of N-edited guanine derivatives from 3,6-diamine-1,2,4-triazin-5-one 44. Conditions: a) S...
Scheme 19: Synthesis of 2-aminoimidazoles 49 by a Mannich-3CR followed by a one-pot intramolecular oxidative a...
Scheme 20: On DNA Suzuki–Miyaura reaction followed by GBB reaction. Conditions: a) CsOH, sSPhos-Pd-G2; b) AcOH...
Scheme 21: One-pot cascade synthesis of 5-iminoimidazoles. Conditions: a) Na2SO4, DMF, 220 °C (MW).
Scheme 22: GBB reaction of 5-amino-1H-imidazole-4-carbonile 57. Conditions: a) HClO4 (5 mol %), MeOH, rt, 24 h....
Scheme 23: One-pot cascade synthesis of indole-imidazo[1,2,a]pyridine hybrids. In blue the structural motif in...
Scheme 24: One-pot cascade synthesis of fused polycyclic indoles 67 or 69 from indole-3-carbaldehyde. Conditio...
Scheme 25: One-pot cascade synthesis of linked- and bridged polycyclic indoles from indole-2-carbaldehyde (70)...
Scheme 26: One-pot cascade synthesis of pentacyclic dihydroisoquinolines (X = N or CH). In blue the structural...
Scheme 27: One-pot stepwise synthesis of imidazopyridine-fused benzodiazepines 85. Conditions: a) p-TsOH (20 m...
Scheme 28: One-pot stepwise synthesis of benzoxazepinium-fused imidazothiazoles 89. Conditions: a) Yb(OTf)3 (2...
Scheme 29: One-pot stepwise synthesis of fused imidazo[4,5,b]pyridines 95. Conditions: a) HClO4, MeOH, rt, ove...
Scheme 30: Synthesis of heterocyclic polymers via the GBB reaction. Conditions: a) p-TsOH, EtOH, 70 °C, 24 h.
Scheme 31: One-pot multicomponent reaction towards the synthesis of covalent organic frameworks via the GBB re...
Scheme 32: One-pot multicomponent reaction towards the synthesis of covalent organic frameworks via the GBB re...
Scheme 33: GBB-like multicomponent reaction towards the synthesis of benzothiazolpyrroles (X = S) and benzoxaz...
Scheme 34: GBB-like multicomponent reaction towards the formation of imidazo[1,2,a]pyridines. Conditions: a) I2...
Scheme 35: Post-functionalization of GBB products via Ugi reaction. Conditions a) HClO4, DMF, rt, 24 h; b) MeO...
Scheme 36: Post-functionalization of GBB products via Click reaction. Conditions: a) solvent-free, 150 °C, 24 ...
Scheme 37: Post-functionalization of GBB products via cascade alkyne–allene isomerization–intramolecular nucle...
Scheme 38: Post-functionalization of GBB products via metal-catalyzed intramolecular N-arylation. In red and b...
Scheme 39: Post-functionalization of GBB products via isocyanide insertion (X = N or CH). Conditions: a) HClO4...
Scheme 40: Post-functionalization of GBB products via intramolecular nucleophilic addition to nitriles. Condit...
Scheme 41: Post-functionalization of GBB products via Pictet–Spengler cyclization. Conditions: a) 4 N HCl/diox...
Scheme 42: Post-functionalization of GBB products via O-alkylation. Conditions: a) TFA (20 mol %), EtOH, 120 °...
Scheme 43: Post-functionalization of GBB products via macrocyclization (X = -CH2CH2O-, -CH2-, -(CH2)4-). Condi...
Figure 1: Antibacterial activity of GBB-Ugi adducts 113 on both Gram-negative and Gram-positive strains.
Scheme 44: GBB multicomponent reaction using trimethoprim as the precursor. Conditions: a) Yb(OTf)3 or Y(OTf)3...
Figure 2: Antibacterial activity of GBB adducts 152 against MRSA and VRE; NA = not available.
Figure 3: Antibacterial activity of GBB adduct 153 against Leishmania amazonensis promastigotes and amastigot...
Figure 4: Antiviral and anticancer evaluation of the GBB adducts 154a and 154b. In vitro antiproliferative ac...
Figure 5: Anticancer activity of the GBB-furoxan hybrids 145b, 145c and 145d determined through antiprolifera...
Scheme 45: Synthesis and anticancer activity of the GBB-gossypol conjugates. Conditions: a) Sc(OTf)3 (10 mol %...
Figure 6: Anticancer activity of polyheterocycles 133a and 136a against human neuroblastoma. Clonogenic assay...
Figure 7: Development of GBB-adducts 158a and 158b as PD-L1 antagonists. HTRF assays were carried out against...
Figure 8: Development of imidazo[1,2-a]pyridines and imidazo[1,2-a]pyrazines as TDP1 inhibitors. The SMM meth...
Figure 9: GBB adducts 164a–c as anticancer through in vitro HDACs inhibition assays. Additional cytotoxic ass...
Figure 10: GBB adducts 165, 166a and 166b as anti-inflammatory agents through HDAC6 inhibition; NA = not avail...
Scheme 46: GBB reaction of triphenylamine 167. Conditions: a) NH4Cl (10 mol %), MeOH, 80 °C (MW), 1 h.
Scheme 47: 1) Modified GBB-3CR. Conditions: a) TMSCN (1.0 equiv), Sc(OTf)3 (0.2 equiv), MeOH, 140 °C (MW), 20 ...
Scheme 48: GBB reaction to assemble imidazo-fused heterocycle dimers 172. Conditions: a) Sc(OTf)3 (20 mol %), ...
Figure 11: Model compounds 173 and 174, used to study the acid/base-triggered reversible fluorescence response...
Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152
Graphical Abstract
Figure 1: Steroidal spiro heterocycles with remarkable pharmacological activity.
Scheme 1: Synthesis of the spirooxetanone 2. a) t-BuOK, THF, rt, 16%.
Scheme 2: Synthesis of the 17-spirooxetane derivative 7. a) HC≡C(CH2)2CH2OTBDPS, n-BuLi, THF, BF3·Et2O, −78 °...
Scheme 3: Pd-catalyzed carbonylation of steroidal alkynols to produce α-methylene-β-lactones at C-3 and C-17 ...
Scheme 4: Catalyst-free protocol to obtain functionalized spiro-lactones by an intramolecular C–H insertion. ...
Scheme 5: One-pot procedure from dienamides to spiro-β-lactams. a) 1. Ac2O, DMAP, Et3N, CH2Cl2, 2. malononitr...
Scheme 6: Spiro-γ-lactone 20 afforded from 7α-alkanamidoestrone derivative 17. a) HC≡CCH2OTHP, n-BuLi, THF, –...
Scheme 7: Synthesis of the 17-spiro-γ-lactone 23, a key intermediate to obtain spironolactone. a) Ethyl propi...
Scheme 8: Synthetic pathway to obtain 17-spirodihydrofuran-3(2H)-ones from 17-oxosteroids. a) 1-Methoxypropa-...
Scheme 9: One-pot procedure to obtain 17-spiro-2H-furan-3-one compounds. a) NaH, diethyl oxalate, benzene, rt...
Scheme 10: Synthesis of 17-spiro-2H-furan-3-one derivatives. a) RCH=NOH, N-chlorosuccinimide/CHCl3, 99%; b) H2...
Scheme 11: Intramolecular condensation of a γ-acetoxy-β-ketoester to synthesize spirofuranone 37. a) (CH3CN)2P...
Scheme 12: Synthesis of spiro 2,5-dihydrofuran derivatives. a) Allyl bromide, DMF, NaH, 0 °C to rt, 93%; b) G-...
Scheme 13: First reported synthesis of C-16 dispiropyrrolidine derivatives. a) Sarcosine, isatin, MeOH, reflux...
Scheme 14: Cycloadducts 47 with antiproliferative activity against human cancer cell lines. a) 1,4-Dioxane–MeO...
Scheme 15: Spiropyrrolidine compounds generated from (E)-16-arylidene steroids and different ylides. a) Acenap...
Scheme 16: 3-Spiropyrrolidines 52a–c obtained from ketones 50a–c. a) p-Toluenesulfonyl hydrazide, MeOH, rt; b)...
Scheme 17: 16-Spiropyrazolines from 16-methylene-13α-estrone derivatives. a) AgOAc, toluene, rt, 78–81%.
Scheme 18: 6-Spiroimidazolines 57 synthesized by a one-pot multicomponent reaction. a) R3-NC, T3P®, DMSO, 70 °...
Scheme 19: Synthesis of spiro-1,3-oxazolines 60, tested as progesterone receptor antagonist agents. a) CF3COCF3...
Scheme 20: Synthesis of spiro-1,3-oxazolidin-2-ones 63 and 66a,b. a) RNH2, EtOH, 70 °C, 70–90%; b) (CCl3O)2CO,...
Scheme 21: Formation of spiro 1,3-oxazolidin-2-one and spiro 2-substituted amino-4,5-dihydro-1,3-oxazoles from ...
Scheme 22: Synthesis of diastereomeric spiroisoxazolines 74 and 75. a) Ar-C(Cl)=N-OH, DIPEA, toluene, rt, 74 (...
Scheme 23: Spiro 1,3-thiazolidine derivatives 77–79 obtained from 2α-bromo-5α-cholestan-3-one 76. a) 2-aminoet...
Scheme 24: Method for the preparation of derivative 83. a) Benzaldehyde, MeOH, reflux, 77%; b) thioglycolic ac...
Scheme 25: Synthesis of spiro 1,3-thiazolidin-4-one derivatives from steroidal ketones. a) Aniline, EtOH, refl...
Scheme 26: Synthesis of spiro N-aryl-1,3-thiazolidin-4-one derivatives 91 and 92. a) Sulfanilamide, DMF, reflu...
Scheme 27: 1,2,4-Trithiolane dimers 94a–e selectively obtained from carbonyl derivatives. a) LR, CH2Cl2, reflu...
Scheme 28: Spiro 1,2,4-triazolidin-3-ones synthesized from semicarbazones. a) H2O2, CHCl3, 0 °C, 82–85%.
Scheme 29: Steroidal spiro-1,3,4-oxadiazoline 99 obtained in two steps from cholest-5-en-3-one (97). a) NH2NHC...
Scheme 30: Synthesis of spiro-1,3,4-thiadiazoline 101 by cyclization and diacetylation of thiosemicarbazone 100...
Scheme 31: Mono- and bis(1,3,4-thiadiazolines) obtained from estrane and androstane derivatives. a) H2NCSNHNH2...
Scheme 32: Different reaction conditions to synthesize spiro-1,3,2-oxathiaphospholanes 108 and 109.
Scheme 33: Spiro-δ-lactones derived from ADT and epi-ADT as inhibitors of 17β-HSDs. a) CH≡C(CH2)2OTHP, n-BuLi,...
Scheme 34: Spiro-δ-lactams 123a,b obtained in a five-step reaction sequence. a) (R)-(+)-tert-butylsulfinamide,...
Scheme 35: Steroid-coumarin conjugates as fluorescent DHT analogues to study 17-oxidoreductases for androgen m...
Scheme 36: 17-Spiro estradiolmorpholinones 130 bearing two types of molecular diversity. a) ʟ- or ᴅ-amino acid...
Scheme 37: Steroidal spiromorpholinones as inhibitors of enzyme 17β-HSD3. a) Methyl ester of ʟ- or ᴅ-leucine, ...
Scheme 38: Steroidal spiro-morpholin-3-ones achieved by N-alkylation or N-acylation of amino diols 141, follow...
Scheme 39: Straightforward method to synthesize a spiromorpholinone derivative from estrone. a) BnBr, K2CO3, CH...
Scheme 40: Pyrazolo[4,3-e][1,2,4]-triazine derivatives 152–154. a) 4-Aminoantipyrine, EtOH/DMF, reflux, 82%; b...
Scheme 41: One-pot procedure to synthesize spiro-1,3,4-thiadiazine derivatives. a) NH2NHCSCONHR, H2SO4, dioxan...
Scheme 42: 1,2,4-Trioxanes with antimalarial activity. a) 1. O2, methylene blue, CH3CN, 500 W tungsten halogen...
Scheme 43: Tetraoxanes 167 and 168 synthesized from ketones 163, 165 and 166. a) NaOH, iPrOH/H2O, 80 °C, 93%; ...
Scheme 44: 1,2,4,5-Tetraoxanes bearing a steroidal moiety and a cycloalkane. a) 30% H2O2/CH2Cl2/CH3CN, HCl, rt...
Scheme 45: Spiro-1,3,2-dioxaphosphorinanes obtained from estrone derivatives. a) KBH4, MeOH, THF or CH2Cl2; b)...
Scheme 46: Synthesis of steroidal spiro-ε-lactone 183. a) 1. Jones reagent, acetone, 0 °C to rt, 2. ClCOCOCl, ...
Scheme 47: Synthesis of spiro-2,3,4,7-tetrahydrooxepines 185 and 187 derived from mestranol and lynestrenol (38...
Beilstein J. Org. Chem. 2024, 20, 1693–1712, doi:10.3762/bjoc.20.151
Graphical Abstract
Scheme 1: Targeted natural products and key enzymatic transformations in the chemo-enzymatic total syntheses ...
Scheme 2: Biosynthetic pathway to brassicicenes in Pseudocercospora fijiensis [14]. (A) Cyclization phase catalyz...
Scheme 3: Chemo-enzymatic total synthesis of cotylenol (1) and brassicicenes. (A) Chemical cyclization phase....
Scheme 4: (A) Biosynthetic pathway for trichodimerol (2) in Penicillium chrysogenum. (B) Chemo-enzymatic tota...
Scheme 5: (A) Proposed biosynthetic pathway for chalcomoracin (3) in Morus alba. (B) Outline of the biosynthe...
Scheme 6: (A) Chemo-enzymatically synthesized natural products by using the originally identified MaDA. (B) M...
Scheme 7: Proposed biosynthetic mechanism of tylactone (4) in Streptomyces fradiae.
Scheme 8: (A) Chemical synthesis and cascade enzymatic transformations of cyclization precursors. (B) Late-st...
Scheme 9: Proposed biosynthetic mechanism of saframycin A (5) in Streptomyces lavendulae.
Scheme 10: (A) Chemo-enzymatic total synthesis of saframycin A (5) and jorunnamycin A (103). (B) Chemo-enzymat...
Beilstein J. Org. Chem. 2024, 20, 1652–1670, doi:10.3762/bjoc.20.147
Graphical Abstract
Figure 1: Schematic representation of the different acceptor regions for the methylation of RiPPs discussed i...
Figure 2: Schematic overview of different methylation strategies for amino acids and peptides. There are seve...
Figure 3: Biological methylation. A) Methyl donors from biological systems. The transferred methyl group is h...
Figure 4: Chemical structures of RiPPs with diverse O-, N-, C-, and S-methylations. Amino acids of lassomycin...
Figure 5: The three-dimensional structures of the conventional O-MTs OlvSA (model structure calculated by Col...
Figure 6: Reaction scheme of the PAMT´s catalysis, leading to the enzymatic conversion of aspartate to aspart...
Figure 7: Structural organisation of the OphMA homodimer. A) Schematic representation. The MT domain is colou...
Figure 8: Overview of the protein architectures and core peptide compositions of borosin N-MTs as defined by ...
Figure 9: Radical SAM C-methyltransferases. A) The different rSAM MT classes containing different functional ...
Figure 10: The three-dimensional structures of the rSAM C-MTs TsrM with bound cobalamin and [4Fe-4S] cluster (...
Beilstein J. Org. Chem. 2024, 20, 1527–1547, doi:10.3762/bjoc.20.137
Graphical Abstract
Figure 1: A) Benzylic fluorides in bioactive compounds, with B) the relative BDEs of different benzylic C–H b...
Figure 2: Base-mediated benzylic fluorination with Selectfluor.
Figure 3: Sonochemical base-mediated benzylic fluorination with Selectfluor.
Figure 4: Mono- and difluorination of nitrogen-containing heteroaromatic benzylic substrates.
Figure 5: Palladium-catalysed benzylic C–H fluorination with N-fluoro-2,4,6-trimethylpyridinium tetrafluorobo...
Figure 6: Palladium-catalysed, PIP-directed benzylic C(sp3)–H fluorination of α-amino acids and proposed mech...
Figure 7: Palladium-catalysed monodentate-directed benzylic C(sp3)–H fluorination of α-amino acids.
Figure 8: Palladium-catalysed bidentate-directed benzylic C(sp3)–H fluorination.
Figure 9: Palladium-catalysed benzylic fluorination using a transient directing group approach. Ratio refers ...
Figure 10: Outline for benzylic C(sp3)–H fluorination via radical intermediates.
Figure 11: Iron(II)-catalysed radical benzylic C(sp3)–H fluorination using Selectfluor.
Figure 12: Silver and amino acid-mediated benzylic fluorination.
Figure 13: Copper-catalysed radical benzylic C(sp3)–H fluorination using NFSI.
Figure 14: Copper-catalysed C(sp3)–H fluorination of benzylic substrates with electrochemical catalyst regener...
Figure 15: Iron-catalysed intramolecular fluorine-atom-transfer from N–F amides.
Figure 16: Vanadium-catalysed benzylic fluorination with Selectfluor.
Figure 17: NDHPI-catalysed radical benzylic C(sp3)–H fluorination with Selectfluor.
Figure 18: Potassium persulfate-mediated radical benzylic C(sp3)–H fluorination with Selectfluor.
Figure 19: Benzylic fluorination using triethylborane as a radical chain initiator.
Figure 20: Heterobenzylic C(sp3)–H radical fluorination with Selectfluor.
Figure 21: Benzylic fluorination of phenylacetic acids via a charge-transfer complex. NMR yields in parenthese...
Figure 22: Oxidative radical photochemical benzylic C(sp3)–H strategies.
Figure 23: 9-Fluorenone-catalysed photochemical radical benzylic fluorination with Selectfluor.
Figure 24: Xanthone-photocatalysed radical benzylic fluorination with Selectfluor II.
Figure 25: 1,2,4,5-Tetracyanobenzene-photocatalysed radical benzylic fluorination with Selectfluor.
Figure 26: Xanthone-catalysed benzylic fluorination in continuous flow.
Figure 27: Photochemical phenylalanine fluorination in peptides.
Figure 28: Decatungstate-photocatalyzed versus AIBN-initiated selective benzylic fluorination.
Figure 29: Benzylic fluorination using organic dye Acr+-Mes and Selectfluor.
Figure 30: Palladium-catalysed benzylic C(sp3)–H fluorination with nucleophilic fluoride.
Figure 31: Manganese-catalysed benzylic C(sp3)–H fluorination with AgF and Et3N·3HF and proposed mechanism. 19...
Figure 32: Iridium-catalysed photocatalytic benzylic C(sp3)–H fluorination with nucleophilic fluoride and N-ac...
Figure 33: Iridium-catalysed photocatalytic benzylic C(sp3)–H fluorination with TBPB HAT reagent.
Figure 34: Silver-catalysed, amide-promoted benzylic fluorination via a radical-polar crossover pathway.
Figure 35: General mechanism for oxidative electrochemical benzylic C(sp3)–H fluorination.
Figure 36: Electrochemical benzylic C(sp3)–H fluorination with HF·amine reagents.
Figure 37: Electrochemical benzylic C(sp3)–H fluorination with 1-ethyl-3-methylimidazolium trifluoromethanesul...
Figure 38: Electrochemical benzylic C(sp3)–H fluorination of phenylacetic acid esters with HF·amine reagents.
Figure 39: Electrochemical benzylic C(sp3)–H fluorination of triphenylmethane with PEG and CsF.
Figure 40: Electrochemical benzylic C(sp3)–H fluorination with caesium fluoride and fluorinated alcohol HFIP.
Figure 41: Electrochemical secondary and tertiary benzylic C(sp3)–H fluorination. GF = graphite felt. DCE = 1,...
Figure 42: Electrochemical primary benzylic C(sp3)–H fluorination of electron-poor toluene derivatives. Ring f...
Figure 43: Electrochemical primary benzylic C(sp3)–H fluorination utilizing pulsed current electrolysis.
Beilstein J. Org. Chem. 2024, 20, 1341–1347, doi:10.3762/bjoc.20.118
Graphical Abstract
Scheme 1: Ullmann and Ullmann-type homo-coupling reactions.
Scheme 2: Rh-catalyzed homo-coupling reactions.
Scheme 3: Rh-catalyzed homo-coupling reaction by using Grignard reagents.
Scheme 4: Rh-catalyzed one-pot Ullmann-type reaction with bromobenzene under optimized reaction conditions.
Figure 1: Scope and limitations for the Rh-catalyzed one-pot Ullmann-type reaction. Conditions: a) The reacti...
Figure 2: Tentative reaction mechanism.
Scheme 5: Synthesis of compound 10n as a candidate for an integrin inhibitor.
Beilstein J. Org. Chem. 2024, 20, 1298–1307, doi:10.3762/bjoc.20.113
Graphical Abstract
Scheme 1: Chemical structures of Cu-tethered tetragonal nanobrackets 1a and 1b.
Scheme 2: Synthesis of nanobracket 4. Reaction conditions: i) XPhos Pd G2, XPhos, B2(OH)4, KOAc, EtOH, 80 °C,...
Figure 1: (a) MALDI-TOF mass spectrum of Cu-nanobrackets 1b, where the inset shows the isotope peaks of [1b]+...
Figure 2: DFT-optimized structure of Cu-nanobrackets (a) 1a and (b) 1b. The yellow regions indicate their sph...
Figure 3: (a) Absorption spectra of Cu-nanobrackets 1b and SWNT extract; (b) Raman spectra of Cu-nanobrackets ...
Figure 4: Raman spectra of HiPco SWNTs, e-, i-, and p-SWNTs (λex = 488 nm) at RBM and G-band regions. Raman i...
Figure 5: (a) Raman spectra of HiPco and extracted SWNTs at 488, 633 and 785 nm excitation wavelengths, norma...
Figure 6: (a) Binding energy between SWNTs of various (n,m)-structures with Cu-nanobrackets 1a and 1b; GFN2-x...
Beilstein J. Org. Chem. 2024, 20, 1246–1255, doi:10.3762/bjoc.20.107
Graphical Abstract
Figure 1: Natural and synthetic compounds containing a quinoline or quinolone core-structure.
Scheme 1: Synthesis of 4. Reaction conditions: i: polyphosphoric acid, 150 °C, 2 h; ii: POBr3 (1.1 equiv), 15...
Scheme 2: Synthesis of compounds 6a–h. Reaction conditions: Pd(PPh3)4 (2.5 mol %), CuI (5 mol %), acetylene (...
Figure 2: ORTEP of 6b (CCDC 2322985).
Scheme 3: Synthesis of 8. Reaction conditions: i: polyphosphoric acid, 150 °C, 2 h [33]; ii: POBr3 (1.1 equiv), 1...
Scheme 4: Synthesis of compounds 9a–g: Reaction conditions: Pd(PPh3)4 (2.5 mol %), CuI (5 mol %), acetylene (...
Figure 3: ORTEP of 9f (CCDC 2322983).
Scheme 5: Synthesis of starting material 11. Reaction conditions: i: AcOH, Br2 (1.1 equiv), reflux, 24 h; ii:...
Scheme 6: Synthesis of compounds 12a–g. Reaction conditions: Pd(PPh3)4 (2.5 mol %), CuI (5 mol %), acetylene ...
Figure 4: ORTEP of 12d (CCDC 2322984).
Figure 5: UV–vis and emission spectra of 6a, 9a and 12a (left) and 12a, 12c, and 12e (right, λex = 380 nm) in...
Beilstein J. Org. Chem. 2024, 20, 1111–1166, doi:10.3762/bjoc.20.98
Graphical Abstract
Scheme 1: General scheme of the borrowing hydrogen (BH) or hydrogen auto-transfer (HA) methodology.
Scheme 2: General scheme for C–N bond formation. A) Traditional cross-couplings with alkyl or aryl halides. B...
Figure 1: Manganese pre-catalysts used for the N-alkylation of amines with alcohols.
Scheme 3: Manganese(I)-pincer complex Mn1 used for the N-alkylation of amines with alcohols and methanol.
Scheme 4: N-Methylation of amines with methanol using Mn2.
Scheme 5: C–N-Bond formation with amines and methanol using PN3P-Mn complex Mn3 reported by Sortais et al. [36]. a...
Scheme 6: Base-assisted synthesis of amines and imines with Mn4. Reaction assisted by A) t-BuOK and B) t-BuON...
Scheme 7: Coupling of alcohols and hydrazine via the HB approach reported by Milstein et al. [38]. aReaction time...
Scheme 8: Proposed mechanism for the coupling of alcohols and hydrazine catalyzed by Mn5.
Scheme 9: Phosphine-free manganese catalyst for N-alkylation of amines with alcohols reported by Balaraman an...
Scheme 10: N-Alkylation of sulfonamides with alcohols.
Scheme 11: Mn–NHC catalyst Mn6 applied for the N-alkylation of amines with alcohols. a3 mol % of Mn6 were used....
Scheme 12: N-Alkylation of amines with primary and secondary alcohols. a80 °C, b100 °C.
Scheme 13: Manganese(III)-porphyrin catalyst for synthesis of tertiary amines.
Scheme 14: Proposed mechanism for the alcohol dehydrogenation with Mn(III)-porphyrin complex Mn7.
Scheme 15: N-Methylation of nitroarenes with methanol using catalyst Mn3.
Scheme 16: Mechanism of manganese-catalyzed methylation of nitroarenes using Mn3 as the catalyst.
Scheme 17: Bidentate manganese complex Mn8 applied for the N-alkylation of primary anilines with alcohols. aOn...
Scheme 18: N-Alkylation of amines with alcohols in the presence of manganese salts and triphenylphosphine as t...
Scheme 19: N-Alkylation of diazo compounds with alcohols using catalyst Mn9.
Scheme 20: Proposed mechanism for the amination of alcohols with diazo compounds catalyzed by catalyst Mn9.
Scheme 21: Mn1 complex-catalyzed synthesis of polyethyleneimine from ethylene glycol and ethylenediamine.
Scheme 22: Bis-triazolylidene-manganese complex Mn10 for the N-alkylation of amines with alcohols.
Figure 2: Manganese complexes applied for C-alkylation reactions of ketones with alcohols.
Scheme 23: General scheme for the C–C bond formation with alcohols and ketones.
Scheme 24: Mn1 complex-catalyzed α-alkylation of ketones with primary alcohols.
Scheme 25: Mechanism for the Mn1-catalyzed alkylation of ketones with alcohols.
Scheme 26: Phosphine-free in situ-generated manganese catalyst for the α-alkylation of ketones with primary al...
Scheme 27: Plausible mechanism for the Mn-catalyzed α-alkylation of ketones with alcohols.
Scheme 28: α-Alkylation of esters, ketones, and amides using alcohols catalyzed by Mn11.
Scheme 29: Mono- and dialkylation of methylene ketones with primary alcohols using the Mn(acac)2/1,10-phenanth...
Scheme 30: Methylation of ketones with methanol and deuterated methanol.
Scheme 31: Methylation of ketones and esters with methanol. a50 mol % of t-BuOK were used, bCD3OD was used ins...
Scheme 32: Alkylation of ketones and secondary alcohols with primary alcohols using Mn4.
Scheme 33: Bidentate manganese-NHC complex Mn6 applied for the synthesis of alkylated ketones using alcohols.
Scheme 34: Mn1-catalyzed synthesis of substituted cycloalkanes by coupling diols and secondary alcohols or ket...
Scheme 35: Proposed mechanism for the synthesis of cycloalkanes via BH method.
Scheme 36: Synthesis of various cycloalkanes from methyl ketones and diols catalyze by Mn13. aReaction time wa...
Scheme 37: N,N-Amine–manganese complex (Mn13)-catalyzed alkylation of ketones with alcohols.
Scheme 38: Naphthyridine‑N‑oxide manganese complex Mn14 applied for the alkylation of ketones with alcohols. a...
Scheme 39: Proposed mechanism of the naphthyridine‑N‑oxide manganese complex (Mn14)-catalyzed alkylation of ke...
Scheme 40: α-Methylation of ketones and indoles with methanol using Mn15.
Scheme 41: α-Alkylation of ketones with primary alcohols using Mn16. aNMR yield.
Figure 3: Manganese complexes used for coupling of secondary and primary alcohols.
Scheme 42: Alkylation of secondary alcohols with primary alcohols catalyzed by phosphine-free catalyst Mn17. a...
Scheme 43: PNN-Manganese complex Mn18 for the alkylation of secondary alcohols with primary alcohols.
Scheme 44: Mechanism for the Mn-pincer catalyzed C-alkylation of secondary alcohols with primary alcohols.
Scheme 45: Upgrading of ethanol with methanol for isobutanol production.
Scheme 46: Mn-Pincer catalyst Mn19 applied for the β-methylation of alcohols with methanol. a2.0 mol % of Mn19...
Scheme 47: Functionalized ketones from primary and secondary alcohols catalyzed by Mn20. aMn20 (5 mol %), NaOH...
Scheme 48: Synthesis of γ-disubstituted alcohols and β-disubstituted ketones through Mn9-catalyzed coupling of...
Scheme 49: Proposed mechanism for the Mn9-catalyzed synthesis of γ-disubstituted alcohols and β-disubstituted ...
Scheme 50: Dehydrogenative coupling of ethylene glycol and primary alcohols catalyzed by Mn4.
Scheme 51: Mn18-cataylzed C-alkylation of unactivated esters and amides with alcohols.
Scheme 52: Alkylation of amides and esters using Mn21.
Scheme 53: α-Alkylation of nitriles with primary alcohols using in situ-generated manganese catalyst.
Scheme 54: Proposed mechanism for the α-alkylation of nitriles with primary alcohols.
Scheme 55: Mn9-catalyzed α-alkylation of nitriles with primary alcohols. a1,4-Dioxane was used as solvent, 24 ...
Figure 4: Manganese complexes used for alkylation of heterocyclic compounds.
Scheme 56: Aminomethylation of aromatic compounds with secondary amines and methanol catalyzed by Mn22.
Scheme 57: Regioselective alkylation of indolines with alcohols catalyzed by Mn9. aMn9 (4 mol %), 48 h.
Scheme 58: Proposed mechanism for the C- and N-alkylation of indolines with alcohols.
Scheme 59: C-Alkylation of methyl N-heteroarenes with primary alcohols catalyzed by Mn1. aTime was 60 h.
Scheme 60: C-Alkylation of oxindoles with secondary alcohols.
Scheme 61: Plausible mechanism for the Mn23-catalyzed C-alkylation of oxindoles with secondary alcohols.
Scheme 62: Synthesis of C-3-alkylated products by coupling alcohols with indoles and aminoalcohols.
Scheme 63: C3-Alkylation of indoles using Mn1.
Scheme 64: C-Methylation of indoles with Mn15 and methanol.
Scheme 65: α-Alkylation of 2-oxindoles with primary and secondary alcohols catalyzed by Mn25. aReaction carrie...
Scheme 66: Dehydrogenative alkylation of indolines with Mn1. aMn1 (5.0 mol %) was used.
Scheme 67: Synthesis of bis(indolyl)methane derivatives from indoles and alcohols catalyzed by Mn26. aMn26 (5....
Scheme 68: One-pot synthesis of pyrimidines via BH.
Scheme 69: Synthesis of pyrroles from alcohols and aminoalcohols using Mn4.
Scheme 70: Synthesis of pyrroles via multicomponent reaction catalyzed by Mn12.
Scheme 71: Friedländer quinoline synthesis using an in situ-generated phosphine-free manganese catalyst.
Scheme 72: Quinoline synthesis using bis-N-heterocyclic carbene-manganese catalyst Mn6.
Scheme 73: Quinoline synthesis using manganese(III)-porphyrin catalyst Mn7.
Scheme 74: Manganese-catalyzed tetrahydroquinoline synthesis via borrowing BH.
Scheme 75: Proposed mechanism for the manganese-catalyzed tetrahydroquinoline synthesis.
Scheme 76: Synthesis of C3-alkylated indoles using Mn24.
Scheme 77: Synthesis of C-3-alkylated indoles using Mn1.
Scheme 78: C–C Bond formation by coupling of alcohols and ylides.
Scheme 79: C-Alkylation of fluorene with alcohols catalyzed by Mn24.
Scheme 80: Proposed mechanism for the C-alkylation of fluorene with alcohols catalyzed by Mn24.
Scheme 81: α-Alkylation of sulfones using Mn-PNN catalyst Mn28.
Beilstein J. Org. Chem. 2024, 20, 1037–1052, doi:10.3762/bjoc.20.92
Graphical Abstract
Figure 1: Chemical structures of H-bonding N-heteroacenes synthesized by Miao et al. and Bunz et al. (a) [22,23]. Pr...
Scheme 1: Synthesis of dicyanopyrazinoquinoxaline derivatives 1a–7a.
Scheme 2: Synthesis of bis-alkoxy-substituted π-conjugated phenanthrolines 16a, 16b, 16c, and 16d.
Scheme 3: An alternative synthetic route to access 7a.
Scheme 4: Synthesis of DPQDs 1b–7b from their corresponding DCPQs 1a–7a. *THF/H2O/1,4-dioxane (4:5:1). **in s...
Figure 2: TGA of 1a–6a (a) and 1b–7b (b) obtained at 10 °C/min under nitrogen.
Figure 3: Absorption spectra (20 μM) for a) DCPQs 1a–6a and b) DPQDs 1b–7b in dimethyl sulfoxide.
Figure 4: Calculated HOMO (below) and LUMO (above) energies by DFT analysis (B3LYP/6-31+G* level of theory), ...
Figure 5: Calculated HOMO (below) and LUMO (above) energies by DFT analysis (B3LYP/6-31+G* level of theory), ...
Figure 6: Asymmetric unit of DPQD 2b with important bond lengths highlighted (a). Torsion angles of 4.33° and...
Beilstein J. Org. Chem. 2024, 20, 973–1000, doi:10.3762/bjoc.20.87
Graphical Abstract
Scheme 1: Pd(0)-catalyzed domino C,N-coupling/carbonylation/Suzuki coupling reaction for the synthesis of 2-a...
Scheme 2: Pd(0)-catalyzed single isonitrile insertion: synthesis of 1-(3-amino)-1H-indol-2-yl)-1-ketones.
Scheme 3: Pd(0)-catalyzed gas-free carbonylation of 2-alkynylanilines to 1-(1H-indol-1-yl)-2-arylethan-1-ones....
Scheme 4: Pd(II)-catalyzed heterocyclization/alkoxycarbonylation of 2-alkynylaniline imines.
Scheme 5: Pd(II)-catalyzed heterocyclization/alkoxycarbonylation of 2-alkynylanilines to N-substituted indole...
Scheme 6: Synthesis of indol-2-acetic esters by Pd(II)-catalyzed carbonylation of 1-(2-aminoaryl)-2-yn-1-ols.
Scheme 7: Pd(II)-catalyzed carbonylative double cyclization of suitably functionalized 2-alkynylanilines to 3...
Scheme 8: Indole synthesis by deoxygenation reactions of nitro compounds reported by Cenini et al. [21].
Scheme 9: Indole synthesis by reduction of nitro compounds: approach reported by Watanabe et al. [22].
Scheme 10: Indole synthesis from o-nitrostyrene compounds as reported by Söderberg and co-workers [23].
Scheme 11: Synthesis of fused indoles (top) and natural indoles present in two species of European Basidiomyce...
Scheme 12: Synthesis of 1,2-dihydro-4(3H)-carbazolones through N-heteroannulation of functionalized 2-nitrosty...
Scheme 13: Synthesis of indoles from o-nitrostyrenes by using Pd(OAc)2 and Pd(tfa)2 in conjunction with bident...
Scheme 14: Synthesis of substituted 3-alkoxyindoles via palladium-catalyzed reductive N-heteroannulation.
Scheme 15: Synthesis of 3-arylindoles by palladium-catalyzed C–H bond amination via reduction of nitroalkenes.
Scheme 16: Synthesis of 2,2′-bi-1H-indoles, 2,3′-bi-1H-indoles, 3,3′-bi-1H-indoles, indolo[3,2-b]indoles, indo...
Scheme 17: Pd-catalyzed reductive cyclization of 1,2-bis(2-nitrophenyl)ethene and 1,1-bis(2-nitrophenyl)ethene...
Scheme 18: Flow synthesis of 2-substituted indoles by reductive carbonylation.
Scheme 19: Pd-catalyzed synthesis of variously substituted 3H-indoles from nitrostyrenes by using Mo(CO)6 as C...
Scheme 20: Synthesis of indoles from substituted 2-nitrostyrenes (top) and ω-nitrostyrenes (bottom) via reduct...
Scheme 21: Synthesis of indoles from substituted 2-nitrostyrenes with formic acid as CO source.
Scheme 22: Ni-catalyzed carbonylative cyclization of 2-nitroalkynes and aryl iodides (top) and the Ni-catalyze...
Scheme 23: Mechanism of the Ni-catalyzed carbonylative cyclization of 2-nitroalkynes and aryl iodides (top) an...
Scheme 24: Route to indole derivatives through Rh-catalyzed benzannulation of heteroaryl propargylic esters fa...
Scheme 25: Pd-catalyzed cyclization of 2-(2-haloaryl)indoles reported by Yoo and co-workers [54], Guo and co-worke...
Scheme 26: Approach for the synthesis of 6H-isoindolo[2,1-a]indol-6-ones reported by Huang and co-workers [57].
Scheme 27: Zhou group’s method for the synthesis of 6H-isoindolo[2,1-a]indol-6-ones.
Scheme 28: Synthesis of 6H-isoindolo[2,1-a]indol-6-ones from o-1,2-dibromobenzene and indole derivatives by us...
Scheme 29: Pd(OAc)2-catalyzed Heck cyclization of 2-(2-bromophenyl)-1-alkyl-1H-indoles reported by Guo et al. [55]....
Scheme 30: Synthesis of indolo[1,2-a]quinoxalinone derivatives through Pd/Cu co-catalyzed carbonylative cycliz...
Scheme 31: Pd-catalyzed carbonylative cyclization of o-indolylarylamines and N-monosubstituted o-indolylarylam...
Scheme 32: Pd-catalyzed diasteroselective carbonylative cyclodearomatization of N-(2-bromobenzoyl)indoles with...
Scheme 33: Pd(0)-catalyzed synthesis of CO-linked heterocyclic scaffolds from alkene-indole derivatives and 2-...
Scheme 34: Proposed mechanism for the Pd(0)-catalyzed synthesis of CO-linked heterocyclic scaffolds.
Scheme 35: Pd-catalyzed C–H and N–H alkoxycarbonylation of indole derivatives to indole-3-carboxylates and ind...
Scheme 36: Rh-catalyzed C–H alcoxycarbonylation of indole derivatives to indole-3-carboxylates reported by Li ...
Scheme 37: Pd-catalyzed C–H alkoxycarbonylation of indole derivatives with alcohols and phenols to indole-3-ca...
Scheme 38: Synthesis of N-methylindole-3-carboxylates from N-methylindoles and phenols through metal-catalyst-...
Scheme 39: Synthesis of indol-3-α-ketoamides (top) and indol-3-amides (bottom) via direct double- and monoamin...
Scheme 40: The direct Sonogashira carbonylation coupling reaction of indoles and alkynes via Pd/CuI catalysis ...
Scheme 41: Synthesis of indole-3-yl aryl ketones reported by Zhao and co-workers [73] (path a) and Zhang and co-wo...
Scheme 42: Pd-catalyzed carbonylative synthesis of BIMs from aryl iodides and N-substituted and NH-free indole...
Scheme 43: Cu-catalyzed direct double-carbonylation and monocarbonylation of indoles and alcohols with hexaket...
Scheme 44: Rh-catalyzed direct C–H alkoxycarbonylation of indoles to indole-2-carboxylates [79] (top) and Co-catal...
Scheme 45: Pd-catalyzed carbonylation of NH free-haloindoles.
Beilstein J. Org. Chem. 2024, 20, 940–949, doi:10.3762/bjoc.20.84
Graphical Abstract
Scheme 1: Examples of drugs containing a γ-lactam and derivative.
Scheme 2: Desymmetrization strategies employing Heck-Matsuda reactions.
Scheme 3: Heck–Matsuda reaction (1) and Jones oxidation (2) of the N-Boc-protected 2,5-dihydro-1H-pyrrole 1a....
Figure 1: N,N-Ligands evaluated in this work.
Scheme 4: Heck–Matsuda reaction of N-tosyl-2,5-dihydro-1H-pyrrole (1b). Reaction conditions: 1) pyrroline 1b ...
Scheme 5: Heck–Matsuda reaction of the protected 2,5-dihydro-1H-pyrrole with Ns and 2-Ns groups (pyrrolines 1c...
Scheme 6: Synthesis of (R)-baclofen hydrochloride (6) from 4dd and (R)-rolipram (5b) from 4de. Reaction condi...
Scheme 7: A rationale for the catalytic cycle for the Heck–Matsuda reaction of the protected 2,5-dihydro-1H-p...
Figure 2: Rationalization of the enantioselectivity obtained in the Heck–Matsuda reaction of protected 2,5-di...
Beilstein J. Org. Chem. 2024, 20, 859–890, doi:10.3762/bjoc.20.78
Graphical Abstract
Figure 1: Scaffolds commonly reported as bioisosteric replacements of para-substituted benzene and examples p...
Figure 2: 1,2-BCPs as isosteres for ortho-and meta-substituted benzenes: comparison of reported exit vector p...
Scheme 1: 1,2-Disubstituted bicyclo[1.1.1]pentanes as isosteres of ortho-substituted benzenes. A: Baran, Coll...
Scheme 2: Synthesis of 1,2-BCPs from BCP 15 by bridge C–H bromination as reported by MacMillan and co-workers ...
Figure 3: Comparative physicochemical data of telmisartan, lomitapide and their BCP isosteres [26,33]. Shake flask d...
Figure 4: 1,2-Disubstituted bicyclo[2.1.1]hexanes as isosteres of ortho-benzenes: Exit vector parameters of t...
Scheme 3: Synthesis of 1,2-disubstituted bicyclo[2.1.1]hexanes via alkene insertion into bicyclo[1.1.0]butane...
Scheme 4: Synthesis of 1,2-disubstituted bicyclo[2.1.1]hexanes via intramolecular crossed [2 + 2] cycloadditi...
Figure 5: Comparison of physicochemical data of fluxapyroxad and boscalid and their 1,2-BCH bioisosteres [36]. Sh...
Figure 6: Antifungal activity of fluxapyroxad, its 1,5-BCH bioisostere (±)-55, boscalid and its bioisostere 1...
Figure 7: 1,5-Disubstituted bicyclo[2.1.1]hexanes as isosteres of ortho-substituted benzenes. Comparison of e...
Scheme 5: Synthesis of 1,5-disubstituted bicyclo[2.1.1]hexanes as isosteres of ortho-benzenes via intramolecu...
Figure 8: Comparison of physicochemical data of fluxapyroxad and boscalid and their 1,5-BCH bioisosteres [45]. Sh...
Figure 9: Antifungal activity of fluxapyroxad, its 1,5-BCH bioisostere (±)-64, boscalid and its bioisostere 1...
Figure 10: 1,5-Disubstituted 3-oxabicylco[2.1.1]hexanes as isosteres for ortho-benzenes: Comparison of exit ve...
Scheme 6: Synthesis of 1,5-disubstituted 3-oxabicyclo[2.1.1]hexanes as isosteres for ortho-benzenes via intra...
Figure 11: Comparison of physicochemical data of fluxapyroxad and boscalid and their 3-oxa-1,5-BCH bioisostere...
Figure 12: Antifungal activity of fluxapyroxad and boscalid and their 3-oxa-1,5-BCH bioisosteres (±)-75 and (±...
Figure 13: 1,2-Disubstituted bicyclo[3.1.1]heptanes as isosteres of ortho-benzenes. Schematic representation o...
Scheme 7: Synthesis of 1,2-disubstituted bicyclo[3.1.1]heptanes as isosteres for ortho-benzenes via alkene in...
Figure 14: 1,2-Disubstituted stellanes as ortho-benzene isosteres: Comparison of selected exit vector paramete...
Scheme 8: Synthesis of 1,2-disubstituted stellanes as isosteres for ortho-benzenes reported by Ryabukhin, Vol...
Figure 15: 1,2-Disubstituted cubanes as ortho-benzene isosteres: Comparison of substituent distances and angle...
Scheme 9: Synthesis of 1,2-disubsituted cubanes as isosteres for ortho-benzenes. A: Synthesis of 1,2-cubane d...
Figure 16: 1,3-Disubstituted bicyclo[2.1.1]hexanes as isosteres of meta-benzenes: comparative exit vector para...
Scheme 10: Synthesis of 1,3-disubstituted bicyclo[2.1.1]hexanes as isosteres for meta-benzenes reported by Wal...
Figure 17: 1,4-Disubstituted bicyclo[2.1.1]hexanes as isosteres of meta-benzenes: comparative exit vector para...
Scheme 11: Synthesis of 1,4-disubstituted bicyclo[2.1.1}hexanes as isosteres for ortho-benzenes via intramolec...
Figure 18: 1,4-Disubstituted-2-oxabicyclo[2.1.1]hexanes as meta-benzene isosteres: comparison of selected exit...
Scheme 12: Synthesis of 1,4-disubstituted 2-oxabicyclo[2.1.1]hexanes as isosteres for meta-benzenes. A: Mykhai...
Figure 19: Comparative physicochemical data for 2- and 3-oxa-1,4-BCHs and para-substituted benzene equivalents...
Figure 20: 1,5-Disubstituted bicyclo[3.1.1]heptanes as isosteres of meta-benzenes: comparison of exit vector p...
Scheme 13: Synthesis of [3.1.1]propellane as a precursor for 1,5-disubsituted bicyclo[3.1.1]heptanes. A: aGass...
Scheme 14: Synthesis of iodine-substituted 1,5-disubstituted bicyclo[3.1.1]heptanes as isosteres for meta-benz...
Scheme 15: Synthesis of nitrogen-, chalcogen- and tin-substituted 1,5-disubstituted bicyclo[3.1.1]heptanes as ...
Figure 21: Comparative physicochemical data of URB597 and 1,5-BCHep isostere 146 [27]. Kinetic aqueous solubility ...
Figure 22: [2]-Ladderanes as isosteres of meta-benzenes: comparison of reported exit vector parameters [63].
Scheme 16: Synthesis of cis-2,6-disubstituted bicyclo[2.2.0]hexanes as isosteres for meta-benzenes. A: Brown a...
Figure 23: Comparative physicochemical data of meta-benzene 158 and [2]-ladderane isostere 159 [63]. Partition coe...
Figure 24: 1,3-Disubstituted cubanes as isosteres of meta-benzenes: comparison of selected exit vector paramet...
Scheme 17: Synthesis of 1,3-disubsituted cubanes as isosteres for meta-benzenes. A: MacMillan and co-workers’ ...
Figure 25: Comparative physicochemical data of lumacaftor and its 1,3-cubane bioisostere 183 [51]. Distribution co...
Figure 26: 1,3-Disubstituted cuneanes as isosteres of meta-benzenes: comparison of selected exit vector parame...
Scheme 18: Synthesis of 1,3-cuneanes as isosteres of meta-benzene. A: Synthesis of 1,3-cuneanes reported by La...
Figure 27: Comparative physicochemical data of sonidegib and its 1,3-cuneane isostere 190 [71]. aSolubility was to...
Figure 28: Exemplary polysubstituted scaffolds related to disubstituted scaffolds suggested as isosteres of or...