Search for "fine chemicals" in Full Text gives 96 result(s) in Beilstein Journal of Organic Chemistry.
Beilstein J. Org. Chem. 2025, 21, 2103–2172, doi:10.3762/bjoc.21.165
Graphical Abstract
Figure 1: C2–C6 biobased carbonyl building blocks.
Scheme 1: Proposed (2 + 2) route to glycolaldehyde and glycolic acid from erythritol by Cu/AC catalyst (AC = ...
Scheme 2: Reductive amination of GCA.
Scheme 3: N-Formylation of secondary amines by reaction with GCA.
Scheme 4: Synthesis and conversion of hydroxy acetals to cyclic acetals.
Scheme 5: Synthesis of 3-(indol-3-yl)-2,3-dihydrofurans via three-component reaction of glycolaldehyde, indol...
Scheme 6: BiCl3-catalyzed synthesis of benzo[a]carbazoles from 2-arylindoles and α-bromoacetaldehyde ethylene...
Scheme 7: Cu/NCNSs-based conversion of glycerol to glycolic acid and other short biobased acids.
Scheme 8: E. coli-based biotransformation of C1 source molecules (CH4, CO2 and CO) towards C2 glycolic acid.
Scheme 9: N-Formylation of amines with C2 (a) or C3 (b) biomass-based feedstocks.
Scheme 10: Methods for the formation of propanoic acid (PA) from lactic acid (LA).
Scheme 11: Co-polymerization of biobased lactic acid and glycolic acid via a bicatalytic process.
Scheme 12: Oxidation of α-hydroxy acids by tetrachloroaurate(III) in acetic acid–sodium acetate buffer medium.
Figure 2: Selective catalytic pathways for the conversion of lactic acid (LA).
Scheme 13: Synthesis of 1,3-PDO via cross-aldol reaction between formaldehyde and acetaldehyde to 3-hydroxypro...
Scheme 14: Hydrothermal conversion of 1,3-dihydroxy-2-propane and 2,3-dihydroxypropanal to methylglyoxal.
Scheme 15: FLS-catalyzed formose reaction to synthesize GA and DHA.
Scheme 16: GCA and DHA oxidation products of glycerol and isomerization of GCA to DHA under flow conditions us...
Scheme 17: Acid-catalyzed reactions of DHA with alcohols.
Scheme 18: Synthesis of dihydroxyacetone phosphate from dihydroxyacetone.
Scheme 19: Bifunctional acid–base catalyst DHA conversion into lactic acid via pyruvaldehyde or fructose forma...
Scheme 20: Catalytic one-pot synthesis of GA and co-synthesis of formamides and formates from DHA.
Scheme 21: (a) Synthesis of furan derivatives and (b) synthesis of thiophene derivative by cascade [3 + 2] ann...
Scheme 22: Brønsted acidic ionic liquid catalyzed synthesis of benzo[a]carbazole from renewable acetol and 2-p...
Scheme 23: Asymmetric hydrogenation of α-hydroxy ketones to 1,2-diols.
Scheme 24: Synthesis of novel 6-(substituted benzylidene)-2-methylthiazolo [2,3-b]oxazol-5(6H)-one from 1-hydr...
Scheme 25: ʟ-Proline-catalyzed synthesis of anti-diols from hydroxyacetone and aldehydes.
Scheme 26: C–C-bond-formation reactions of a biomass-based feedstock aromatic aldehyde (C5) and hydroxyacetone...
Scheme 27: Ethanol upgrading to C4 bulk chemicals via the thiamine (VB1)-catalyzed acetoin condensation.
Scheme 28: One-pot sequential chemoenzymatic synthesis of 2-aminobutane-1,4-diol and 1,2,4-butanetriol via 1,4...
Scheme 29: Synthesis of 1,4-dihydroxybutan-2-one by microbial transformation.
Scheme 30: Conversion of polyols by [neocuproine)Pd(OAc)]2(OTf)2] to α-hydroxy ketones.
Scheme 31: Chemoselective oxidation of alcohols with chiral palladium-based catalyst 2.
Scheme 32: Electrochemical transformation of furfural to 5-hydroxy-2(5H)-furanone (HFO).
Scheme 33: Selective hydrodeoxygenation of HFO and oxidation to γ-butyrolactone (GBL).
Scheme 34: Photosensitized oxygenation of furan towards HFO via ozonide intermediates.
Scheme 35: Conversion of furfural to HFO and MAN by using mesoporous carbon nitride (SGCN) as photocatalyst.
Scheme 36: Synthesis of HFO from furan derivatives.
Scheme 37: Photooxidation of furfural to 5-hydroxy-2(5H)-furanone (HFO).
Scheme 38: Synthesis of Friedel–Crafts indole adduct from HFO.
Scheme 39: Conversion of HFO to α,γ-substituted chiral γ-lactones.
Scheme 40: Tautomeric transformation of HFO to formylacrylic acid.
Scheme 41: Hydrolysis of HFO to succinic acid in aqueous solution.
Scheme 42: Substitution and condensation reactions of 5-hydroxy-2(5H)-furanone (HFO).
Scheme 43: (a) Conversion of HFO towards valuable C4 chemicals and (b) anodic oxidation of 5-hydroxy-2(5H)-fur...
Figure 3: Conversion of HFO towards other natural and synthetic substances.
Scheme 44: Conversion of furfural to maleic anhydride (reaction a: VOx/Al2O3; reaction b: VPO).
Scheme 45: Conversion of furfural into succinic acid.
Scheme 46: Electro‑, photo‑, and biocatalysis for one-pot selective conversions of furfural into C4 chemicals.
Scheme 47: Production route of furfural from hemicellulose.
Scheme 48: Mechanism for xylose dehydration to furfural through a choline xyloside intermediate.
Scheme 49: Conversion of furfural to furfuryl alcohol and its derivatives.
Scheme 50: Conversion of furfural to furfuryl alcohol and 3-(2-furyl)acrolein.
Scheme 51: The aerobic oxidative condensation of biomass-derived furfural and linear alcohols.
Scheme 52: The single-step synthesis of 2-pentanone from furfural.
Scheme 53: Electrocatalytic coupling reaction of furfural and levulinic acid.
Scheme 54: Conversion of furfural to m-xylylenediamine.
Scheme 55: Conversion of furfural to tetrahydrofuran-derived amines.
Scheme 56: Formation of trans-4,5-diamino-cyclopent-2-enones from furfural.
Scheme 57: Production of pyrrole and proline from furfural.
Scheme 58: Synthesis of 1‑(trifluoromethyl)-8-oxabicyclo[3.2.1]oct-3-en-2-ones from furfural.
Scheme 59: Conversion of furfural to furfural-derived diacids.
Scheme 60: A telescope protocol derived from furfural and glycerol.
Scheme 61: A tandem cyclization of furfural and 5,5-dimethyl-1,3-cyclohexanedione.
Scheme 62: A Ugi four-component reaction to construct furfural-based polyamides.
Scheme 63: One-pot synthesis of γ-acyloxy-Cy7 from furfural.
Scheme 64: Dimerization–Piancatelli sequence toward humins precursors from furfural.
Scheme 65: Conversion of furfural to CPN.
Scheme 66: Synthesis of jet fuels range cycloalkanes from CPN and lignin-derived vanillin.
Scheme 67: Solar-energy-driven synthesis of high-density biofuels from CPN.
Scheme 68: Reductive amination of CPN to cyclopentylamine.
Scheme 69: Asymmetric hydrogenation of C=O bonds of exocyclic α,β-unsaturated cyclopentanones.
Scheme 70: Preparation of levulinic acid via the C5 route (route a) or C6 route (routes b1 and b2).
Scheme 71: Mechanism of the rehydration of HMF to levulinic acid and formic acid.
Scheme 72: Important levulinic acid-derived chemicals.
Scheme 73: Direct conversion of levulinic acid to pentanoic acid.
Scheme 74: Catalytic aerobic oxidation of levulinic acid to citramalic acid.
Scheme 75: Conversion of levulinic acid to 1,4-pentanediol (a) see ref. [236]; b) see ref. [237]; c) see ref. [238]; d) see r...
Scheme 76: Selective production of 2-butanol through hydrogenolysis of levulinic acid.
Scheme 77: General reaction pathways proposed for the formation of 5MPs from levulinic acid.
Scheme 78: Selective reductive amination of levulinic acid to N-substituted pyrroles.
Scheme 79: Reductive amination of levulinic acid to chiral pyrrolidinone.
Scheme 80: Reductive amination of levulinic acid to non-natural chiral γ-amino acid.
Scheme 81: Nitrogen-containing chemicals derived from levulinic acid.
Scheme 82: Preparation of GVL from levulinic acid by dehydration and hydrogenation.
Scheme 83: Ruthenium-catalyzed levulinic acid to chiral γ-valerolactone.
Scheme 84: Catalytic asymmetric hydrogenation of levulinic acid to chiral GVL.
Scheme 85: Three steps synthesis of ε-caprolactam from GVL.
Scheme 86: Multistep synthesis of nylon 6,6 from GVL.
Scheme 87: Preparation of MeGVL by α-alkylation of GVL.
Scheme 88: Ring-opening polymerization of five-membered lactones.
Scheme 89: Synthesis of GVL-based ionic liquids.
Scheme 90: Preparation of butene isomers from GVL under Lewis acid conditions.
Scheme 91: Construction of C5–C12 fuels from GVL over nano-HZSM-5 catalysts.
Scheme 92: Preparation of alkyl valerate from GVL via ring opening/reduction/esterification sequence.
Scheme 93: Construction of 4-acyloxypentanoic acids from GVL.
Scheme 94: Synthesis of 1,4-pentanediol (PDO) from GVL.
Scheme 95: Construction of novel cyclic hemiketal platforms via self-Claisen condensation of GVL.
Scheme 96: Copper-catalyzed lactamization of GVL.
Figure 4: Main scaffolds obtained from HMF.
Scheme 97: Biginelli reactions towards HMF-containing dihydropyrimidinones.
Scheme 98: Hantzsch dihydropyridine synthesis involving HMF.
Scheme 99: The Kabachnik–Fields reaction involving HMF.
Scheme 100: Construction of oxazolidinone from HMF.
Scheme 101: Construction of rhodamine-furan hybrids from HMF.
Scheme 102: A Groebke–Blackburn–Bienaymé reaction involving HMF.
Scheme 103: HMF-containing benzodiazepines by [4 + 2 + 1] cycloadditions.
Scheme 104: Synthesis of fluorinated analogues of α-aryl ketones.
Scheme 105: Synthesis of HMF derived disubstituted γ-butyrolactone.
Scheme 106: Functionalized aromatics from furfural and HMF.
Scheme 107: Diels–Alder adducts from HMF or furfural with N-methylmaleimide.
Scheme 108: Pathway of the one-pot conversion of HMF into phthalic anhydride.
Scheme 109: Photocatalyzed preparation of humins (L-H) from HMF mixed with spoiled HMF residues (LMW-H) and fur...
Scheme 110: Asymmetric dipolar cycloadditions on HMF.
Scheme 111: Dipolar cycloadditions of HMF based nitrones to 3,4- and 3,5-substituted isoxazolidines.
Scheme 112: Production of δ-lactone-fused cyclopenten-2-ones from HMF.
Scheme 113: Aza-Piancatelli access to aza-spirocycles from HMF-derived intermediates.
Scheme 114: Cross-condensation of furfural, acetone and HMF into C13, C14 and C15 products.
Scheme 115: Base-catalyzed aldol condensation/dehydration sequences from HMF.
Scheme 116: Condensation of HMF and active methylene nitrile.
Scheme 117: MBH reactions involving HMF.
Scheme 118: Synthesis of HMF-derived ionic liquids.
Scheme 119: Reductive amination/enzymatic acylation sequence towards HMF-based surfactants.
Scheme 120: The formation of 5-chloromethylfurfural (CMF).
Scheme 121: Conversion of CMF to HMF, levulinic acid, and alkyl levulinates.
Scheme 122: Conversion of CMF to CMFCC and FDCC.
Scheme 123: Conversion of CMF to BHMF.
Scheme 124: Conversion of CMF to DMF.
Scheme 125: CMF chlorine atom substitutions toward HMF ethers and esters.
Scheme 126: Introduction of carbon nucleophiles in CMF.
Scheme 127: NHC-catalyzed remote enantioselective Mannich-type reactions of CMF.
Scheme 128: Conversion of CMF to promising biomass-derived dyes.
Scheme 129: Radical transformation of CMF with styrenes.
Scheme 130: Synthesis of natural herbicide δ-aminolevulinic acid from CMF.
Scheme 131: Four step synthesis of the drug ranitidine from CMF.
Scheme 132: Pd/CO2 cooperative catalysis for the production of HHD and HXD.
Scheme 133: Different ruthenium (Ru) catalysts for the ring-opening of 5-HMF to HHD.
Scheme 134: Proposed pathways for preparing HXD from HMF.
Scheme 135: MCP formation and uses.
Scheme 136: Cu(I)-catalyzed highly selective oxidation of HHD to 2,5-dioxohexanal.
Scheme 137: Synthesis of N‑substituted 3‑hydroxypyridinium salts from 2,5-dioxohexanal.
Scheme 138: Ru catalyzed hydrogenations of HHD to 1,2,5-hexanetriol (a) see ref. [396]; b) see ref. [397]).
Scheme 139: Aviation fuel range quadricyclanes produced by HXD.
Scheme 140: Synthesis of HDGK from HXD and glycerol as a chain extender.
Scheme 141: Synthesis of serinol pyrrole from HXD and serinol.
Scheme 142: Synthesis of pyrroles from HXD and nitroarenes.
Scheme 143: Two-step production of PX from cellulose via HXD.
Scheme 144: Preparation of HCPN from HMF via hydrogenation and ring rearrangement.
Scheme 145: Suggested pathways from HMF to HCPN.
Scheme 146: α-Alkylation of HCPN with ethylene gas.
Scheme 147: Synthesis of 3-(hydroxymethyl)cyclopentylamine from HMF via reductive amination of HCPN.
Scheme 148: Production of LGO and Cyrene® from biomass.
Scheme 149: Synthesis of HBO from LGO and other applications.
Scheme 150: Construction of m-Cyrene® homopolymer.
Scheme 151: Conversion of Cyrene® to THFDM and 1,6-hexanediol.
Scheme 152: RAFT co-polymerization of LGO and butadienes.
Scheme 153: Polycondensation of HO-LGOL and diols with dimethyl adipate.
Scheme 154: Self-condensation of Cyrene® and Claisen–Schmidt reactions.
Scheme 155: Synthesis of 5-amino-2-(hydroxymethyl)tetrahydropyran from Cyrene®.
Beilstein J. Org. Chem. 2025, 21, 1678–1699, doi:10.3762/bjoc.21.132
Graphical Abstract
Figure 1: Three key dimensions of a complete nitration process.
Figure 2: A typical continuous-flow nitration reaction system.
Figure 3: Corrosion characteristics of common wetted materials used in continuous-flow nitration system. Note...
Figure 4: Analysis of the literature on continuous-flow nitration reaction over the past decade.
Scheme 1: Model reaction for the homogeneous nitration by nitric acid/mixed acid.
Figure 5: Safety assessment criteria for nitration reactions. Notes: apressure-independent; bno hazards arisi...
Figure 6: Guide for the investigation of continuous-flow nitration processes.
Beilstein J. Org. Chem. 2025, 21, 1374–1387, doi:10.3762/bjoc.21.102
Graphical Abstract
Figure 1: Simplified schematic rendering of a high hydrostatic pressure reactor.
Scheme 1: High pressure-initiated synthesis of 1,3-dihydrobenzimidazoles 3a–d. The yields are GC yields and t...
Figure 2: Illustration of the cyclization reaction between chalcone (4) and 3-(trifluoromethyl)phenylhydrazin...
Scheme 2: High pressure-initiated catalyst- and solvent-free synthesis of pyrazoles 6a–c from chalcone (4) an...
Figure 3: Schematic representation of the cycling experiments: the major variables are the applied pressure, ...
Scheme 3: High pressure-initiated synthesis of the active pharmaceutical ingredients in Tylenol® and Aspirin®...
Scheme 4: High pressure-initiated esterification of alcohols 12a–g in a catalyst- and additional solvent-free...
Scheme 5: High pressure-initiated large scale syntheses of N-aryl- and N-alkylpyrroles at about 100 g scale.
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, 2129–2142, doi:10.3762/bjoc.20.183
Graphical Abstract
Scheme 1: Esterification of oleic acid (1) with propylsulfonic acid (Pr-SO3H)-functionalised mesoporous silic...
Scheme 2: Using confinement of organocatalytic units for improving the enantioselectivity of silica-supported...
Scheme 3: Michael addition catalysed by cinchona thiourea immobilised on magnetic nanoparticles (13).
Scheme 4: Michael addition catalysed by cinchona thiourea in the presence of magnetic nanoparticles.
Scheme 5: Benzoin condensation catalysed by N-benzylthiazolium salt attached to mesoporous material.
Scheme 6: Photoinduced RAFT polymerisation of n-butyl acrylate (19) catalysed by silica nanoparticle-supporte...
Scheme 7: Pressure and temperature dependence of the 1,4-addition of propanal to trans-β-nitrostyrene under c...
Scheme 8: α-Amination of ethyl 2-oxocyclopentanecarboxylate catalysed by PS-THU which could be recycled over ...
Scheme 9: Preparation of supported catalysts C29–C31 from cinchona squaramides 29–31 modified with a primary ...
Scheme 10: Application of PGMA-supported organocatalysts C29–C31 in the asymmetric Michael addition of pentane...
Scheme 11: Alcoholytic desymmetrisation of a cyclic anhydride 34 catalysed by polyamide-supported cinchona sul...
Beilstein J. Org. Chem. 2024, 20, 1468–1475, doi:10.3762/bjoc.20.130
Graphical Abstract
Scheme 1: Synthesis of aniline derivatives from 2-cyclohexenones or derivatives thereof.
Scheme 2: Synthesis of (E)-2-arylidene-3-cyclohexenones 2.
Scheme 3: Substrate scope of (E)-2-arylidene-3-cyclohexenones 2. Conditions: reactions were conducted with 2a...
Scheme 4: Substrate scope of primary amines 3. Conditions: reactions conducted with 2 (0.2 mmol) and 3b–y (2....
Scheme 5: Gram-scale reaction and successive one-pot synthesis.
Scheme 6: Synthetic manipulation.
Beilstein J. Org. Chem. 2024, 20, 1376–1395, doi:10.3762/bjoc.20.120
Graphical Abstract
Figure 1: Types and mechanism of the Cannizzaro reaction.
Figure 2: Various approaches of the Cannizzaro reaction.
Figure 3: Representative molecules synthesized via the Cannizzaro reaction.
Scheme 1: Intramolecular Cannizzaro reaction of aryl glyoxal hydrates using TOX catalysts.
Scheme 2: Intramolecular Cannizzaro reaction of aryl methyl ketones using ytterbium triflate/selenium dioxide....
Scheme 3: Intramolecular Cannizzaro reaction of aryl glyoxals using Cr(ClO4)3 as catalyst.
Scheme 4: Cu(II)-PhBox-catalyzed asymmetric Cannizzaro reaction.
Scheme 5: FeCl3-based chiral catalyst applied for the enantioselective intramolecular Cannizzaro reaction rep...
Scheme 6: Copper bis-oxazoline-catalysed intramolecular Cannizzaro reaction and proposed mechanism.
Scheme 7: Chiral Fe catalysts-mediated enantioselective Cannizzaro reaction.
Scheme 8: Ruthenium-catalyzed Cannizzaro reaction of aromatic aldehydes.
Scheme 9: MgBr2·Et2O-assisted Cannizzaro reaction of aldehydes.
Scheme 10: LiBr-catalyzed intermolecular Cannizzaro reaction of aldehydes.
Scheme 11: γ-Alumina as a catalyst in the Cannizzaro reaction.
Scheme 12: AlCl3-mediated Cannizzaro disproportionation of aldehydes.
Scheme 13: Ru–N-heterocyclic carbene catalyzed dehydrogenative synthesis of carboxylic acids.
Figure 4: Proposed catalytic cycle for the dehydrogenation of alcohols.
Scheme 14: Intramolecular desymmetrization of tetraethylene glycol.
Scheme 15: Desymmetrization of oligoethylene glycol dialdehydes.
Scheme 16: Intramolecular Cannizzaro reaction of calix[4]arene dialdehydes.
Scheme 17: Desymmetrization of dialdehydes of symmetrical crown ethers using Ba(OH)2.
Scheme 18: Synthesis of ottelione A (proposed) via intramolecular Cannizzaro reaction.
Scheme 19: Intramolecular Cannizzaro reaction for the synthesis of pestalalactone.
Scheme 20: Synthetic strategy towards nigricanin involving an intramolecular Cannizzaro reaction.
Scheme 21: Spiro-β-lactone-γ-lactam part of oxazolomycins via aldol crossed-Cannizzaro reaction.
Scheme 22: Synthesis of indole alkaloids via aldol crossed-Cannizzaro reaction.
Scheme 23: Aldol and crossed-Cannizzaro reaction towards the synthesis of ertuliflozin.
Scheme 24: Synthesis of cyclooctadieneones using a Cannizzaro reaction.
Scheme 25: Microwave-assisted crossed-Cannizzaro reaction for the synthesis of 3,3-disubstituted oxindoles.
Scheme 26: Synthesis of porphyrin-based rings using the Cannizzaro reaction.
Scheme 27: Synthesis of phthalides and pestalalactone via Cannizarro–Tishchenko-type reaction.
Scheme 28: Synthesis of dibenzoheptalene bislactones via a double intramolecular Cannizzaro reaction.
Beilstein J. Org. Chem. 2024, 20, 841–851, doi:10.3762/bjoc.20.76
Graphical Abstract
Scheme 1: Arylation reactions of aromatic compounds and reaction patterns of ortho-functionalized diaryliodon...
Scheme 2: Mechanism study. Standard conditions: 1 (0.3 mmol, 1 equiv), 2 (0.33 mmol, 1.1 equiv), Cu(OAc)2 (10...
Beilstein J. Org. Chem. 2023, 19, 1028–1046, doi:10.3762/bjoc.19.79
Graphical Abstract
Scheme 1: Synthesis of the compounds. Conditions: (a) 4-fluoroaniline, acetic acid, N2, reflux, 7 h, yield: 7...
Figure 1: UV–vis absorption spectra of (a) NI-PTZ-F, NI-PTZ-Ph, NI-PTZ-CH3, NI-PTZ-OCH3, and NI-PTZ-C5 and (b...
Figure 2: Fluorescence spectra of the dyads. (a) NI-PTZ-F, (b) NI-PTZ-Ph, (c) NI-PTZ-CH3, (d) NI-PTZ-OCH3, (e...
Figure 3: Fluorescence spectra of the dyads. (a) NI-PTZ-F, (b) NI-PTZ-Ph, (c) NI-PTZ-CH3, (d) NI-PTZ-OCH3, (e...
Figure 4: Fluorescence lifetime of (a) NI-PTZ-F; (b) NI-PTZ-Ph; (c) NI-PTZ-CH3; (d) NI-PTZ-OCH3 (λem = 610 nm...
Figure 5: Cyclic voltammograms of the compounds. (a) NI-PTZ-F; NI-PTZ-Ph; NI-PTZ-CH3; NI-PTZ-OCH3; NI-PTZ-C5 ...
Figure 6: Thermogravimetric analysis curves of NI-PTZ-F, NI-PTZ-Ph, NI-PTZ-CH3, NI-PTZ-OCH3, NI-PTZ-F-O, and ...
Figure 7: Femtosecond transient absorption spectra of NI-PTZ-F. (a) Transient absorption spectra and (b) the ...
Figure 8: Nanosecond transient absorption spectra of NI-PTZ-F in deaerated solvents of (a) HEX (c = 2.0 × 10−5...
Figure 9: Nanosecond transient absorption spectra of (a) NI-PTZ-F-O (c = 4.0 × 10−5 M), (b) NI-PTZ-Ph-O (c = ...
Figure 10: Optimized ground state geometry of (a) NI-PTZ-F, (b) NI-PTZ-Ph, (c) NI-PTZ-CH3, (d) NI-PTZ-OCH3, (e...
Figure 11: Spin density surfaces of the dyads in the T1 state (gas phase) of (a) NI-PTZ-F, (b) NI-PTZ-Ph, (c) ...
Figure 12: Selected frontier molecular orbitals of NI-PTZ-F, NI-PTZ-Ph, NI-PTZ-C5, NI-PTZ-F-O, NI-PTZ-Ph-O, an...
Scheme 2: Simplified Jablonski diagram of (a) NI-PTZ-F and (b) NI-PTZ-F-O. The 1LE state (1[NI–PTZ–F–O]*) ene...
Beilstein J. Org. Chem. 2023, 19, 33–35, doi:10.3762/bjoc.19.3
Beilstein J. Org. Chem. 2022, 18, 1435–1453, doi:10.3762/bjoc.18.149
Beilstein J. Org. Chem. 2022, 18, 1154–1158, doi:10.3762/bjoc.18.119
Graphical Abstract
Figure 1: (a) Cyclic voltammograms of a BDD electrode in MeCN solution containing cumene (1; 5 mM) and Et4NClO...
Figure 2: Proposed reaction mechanism of electro-conversion of cumene (1) into acetophenone (3).
Beilstein J. Org. Chem. 2022, 18, 1032–1039, doi:10.3762/bjoc.18.104
Graphical Abstract
Scheme 1: The synthesis of formamides and monomethylamines.
Scheme 2: The possible reaction mechanism. RDS = rate determining step.
Beilstein J. Org. Chem. 2022, 18, 754–768, doi:10.3762/bjoc.18.76
Graphical Abstract
Figure 1: The olfactory spectrum wheel ordering different types of odorants from fruity to musky.
Figure 2: Classification of odorants as “top note”, “middle note” and “base note” depending on their substant...
Scheme 1: Synthesis of raspberry ketone (5) and raspberry ketone methyl ether (6) in two steps in flow.
Scheme 2: Autoxidation of (+)-valencene (7) to (+)-nootkatone (8) under catalyst and solvent-free conditions ...
Scheme 3: Enzyme-catalyzed acetylation of isoamyl alcohol (9) in a biphasic n-heptane/water mixture utilizing...
Scheme 4: Esterification of alcohols by transesterification, catalyzed by immobilized acyltransferase in a pa...
Scheme 5: Synthesis of homologated alcohols 20 by iterative homologation of terpenyl boronate esters 17 follo...
Scheme 6: Sequential three-step synthesis of (S)-α-phellandrene (30) from (R)-carvone (25) via selective hydr...
Scheme 7: Selective hydrogenation of alkyne 31 to “leaf alcohol” 32 employing a solid-supported palladium cat...
Scheme 8: A) Synthesis of jasmonal (35) by crossed aldol condensation of benzaldehyde (33) and heptanal (34) ...
Scheme 9: Synthesis of thymol (41) from m-cresol (39) and isopropyl alcohol via Fries-type rearrangement of e...
Scheme 10: Preparation of coumarin (46) by reaction of salicylaldehyde (44) with potassium acetate, acetic aci...
Scheme 11: Synthesis of phthalide (50) by photoinduced decatungstate catalysis.
Scheme 12: Synthesis of woody acetate (54) by reduction of cyclohexanone 51 and subsequent acetylation; ADH200...
Scheme 13: Synthesis of juniper lactone (56) by pyrolysis of triperoxide 55 generated by oxidation of cyclohex...
Scheme 14: Synthesis of macrocyclic olefine 60 by ring-closing metathesis of diene 58 in a continuously stirre...
Scheme 15: Synthesis of macrocycles 65 and 66 by ring-closing metathesis of dienes 62 or 63, respectively, in ...
Scheme 16: Z-Selective synthesis of civetone (69) enabled by metathesis catalyst 68 in a tube-in-tube reactor.
Scheme 17: Synthesis of macrocyclic olefine 72 by ring-closing metathesis of diene 70.
Beilstein J. Org. Chem. 2022, 18, 167–173, doi:10.3762/bjoc.18.18
Graphical Abstract
Figure 1: Model of the catalyst action.
Figure 2: Catalysts screened.
Scheme 1: Screening of different N-protecting groups. Reaction conditions: 0.2 M solution of 1 (1 equiv), 2 (...
Scheme 2: Scope of the reaction (the relative configuration of the major diastereoisomer is depicted). Reacti...
Scheme 3: Comparison reactions of E- and Z-isomers (the relative configurations of the major diastereoisomers...
Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196
Graphical Abstract
Figure 1: Price comparison among iron and other transition metals used in catalysis.
Scheme 1: Typical modes of C–C bond formation.
Scheme 2: The components of an iron-catalyzed domino reaction.
Scheme 3: Iron-catalyzed tandem cyclization and cross-coupling reactions of iodoalkanes 1 with aryl Grignard ...
Scheme 4: Three component iron-catalyzed dicarbofunctionalization of vinyl cyclopropanes 14.
Scheme 5: Three-component iron-catalyzed dicarbofunctionalization of alkenes 21.
Scheme 6: Double carbomagnesiation of internal alkynes 31 with alkyl Grignard reagents 32.
Scheme 7: Iron-catalyzed cycloisomerization/cross-coupling of enyne derivatives 35 with alkyl Grignard reagen...
Scheme 8: Iron-catalyzed spirocyclization/cross-coupling cascade.
Scheme 9: Iron-catalyzed alkenylboration of alkenes 50.
Scheme 10: N-Alkyl–N-aryl acrylamide 60 CDC cyclization with C(sp3)–H bonds adjacent to a heteroatom.
Scheme 11: 1,2-Carboacylation of activated alkenes 60 with aldehydes 65 and alcohols 67.
Scheme 12: Iron-catalyzed dicarbonylation of activated alkenes 68 with alcohols 67.
Scheme 13: Iron-catalyzed cyanoalkylation/radical dearomatization of acrylamides 75.
Scheme 14: Synergistic photoredox/iron-catalyzed 1,2-dialkylation of alkenes 82 with common alkanes 83 and 1,3...
Scheme 15: Iron-catalyzed oxidative coupling/cyclization of phenol derivatives 86 and alkenes 87.
Scheme 16: Iron-catalyzed carbosulfonylation of activated alkenes 60.
Scheme 17: Iron-catalyzed oxidative spirocyclization of N-arylpropiolamides 91 with silanes 92 and tert-butyl ...
Scheme 18: Iron-catalyzed free radical cascade difunctionalization of unsaturated benzamides 94 with silanes 92...
Scheme 19: Iron-catalyzed cyclization of olefinic dicarbonyl compounds 97 and 100 with C(sp3)–H bonds.
Scheme 20: Radical difunctionalization of o-vinylanilides 102 with ketones and esters 103.
Scheme 21: Dehydrogenative 1,2-carboamination of alkenes 82 with alkyl nitriles 76 and amines 105.
Scheme 22: Iron-catalyzed intermolecular 1,2-difunctionalization of conjugated alkenes 107 with silanes 92 and...
Scheme 23: Four-component radical difunctionalization of chemically distinct alkenes 114/115 with aldehydes 65...
Scheme 24: Iron-catalyzed carbocarbonylation of activated alkenes 60 with carbazates 117.
Scheme 25: Iron-catalyzed radical 6-endo cyclization of dienes 119 with carbazates 117.
Scheme 26: Iron-catalyzed decarboxylative synthesis of functionalized oxindoles 130 with tert-butyl peresters ...
Scheme 27: Iron‑catalyzed decarboxylative alkylation/cyclization of cinnamamides 131/134.
Scheme 28: Iron-catalyzed carbochloromethylation of activated alkenes 60.
Scheme 29: Iron-catalyzed trifluoromethylation of dienes 142.
Scheme 30: Iron-catalyzed, silver-mediated arylalkylation of conjugated alkenes 115.
Scheme 31: Iron-catalyzed three-component carboazidation of conjugated alkenes 115 with alkanes 101/139b and t...
Scheme 32: Iron-catalyzed carboazidation of alkenes 82 and alkynes 160 with iodoalkanes 20 and trimethylsilyl ...
Scheme 33: Iron-catalyzed asymmetric carboazidation of styrene derivatives 115.
Scheme 34: Iron-catalyzed carboamination of conjugated alkenes 115 with alkyl diacyl peroxides 163 and acetoni...
Scheme 35: Iron-catalyzed carboamination using oxime esters 165 and arenes 166.
Scheme 36: Iron-catalyzed iminyl radical-triggered [5 + 2] and [5 + 1] annulation reactions with oxime esters ...
Scheme 37: Iron-catalyzed decarboxylative alkyl etherification of alkenes 108 with alcohols 67 and aliphatic a...
Scheme 38: Iron-catalyzed inter-/intramolecular alkylative cyclization of carboxylic acid and alcohol-tethered...
Scheme 39: Iron-catalyzed intermolecular trifluoromethyl-acyloxylation of styrene derivatives 115.
Scheme 40: Iron-catalyzed carboiodination of terminal alkenes and alkynes 180.
Scheme 41: Copper/iron-cocatalyzed cascade perfluoroalkylation/cyclization of 1,6-enynes 183/185.
Scheme 42: Iron-catalyzed stereoselective carbosilylation of internal alkynes 187.
Scheme 43: Synergistic photoredox/iron catalyzed difluoroalkylation–thiolation of alkenes 82.
Scheme 44: Iron-catalyzed three-component aminoazidation of alkenes 82.
Scheme 45: Iron-catalyzed intra-/intermolecular aminoazidation of alkenes 194.
Scheme 46: Stereoselective iron-catalyzed oxyazidation of enamides 196 using hypervalent iodine reagents 197.
Scheme 47: Iron-catalyzed aminooxygenation for the synthesis of unprotected amino alcohols 200.
Scheme 48: Iron-catalyzed intramolecular aminofluorination of alkenes 209.
Scheme 49: Iron-catalyzed intramolecular aminochlorination and aminobromination of alkenes 209.
Scheme 50: Iron-catalyzed intermolecular aminofluorination of alkenes 82.
Scheme 51: Iron-catalyzed aminochlorination of alkenes 82.
Scheme 52: Iron-catalyzed phosphinoylazidation of alkenes 108.
Scheme 53: Synergistic photoredox/iron-catalyzed three-component aminoselenation of trisubstituted alkenes 82.
Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126
Graphical Abstract
Scheme 1: Schematic overview of transition metals studied in C–H activation processes.
Scheme 2: (A) Known biological activities related to benzimidazole-based compounds; (B and C) an example of a...
Scheme 3: (A) Known biological activities related to quinoline-based compounds; (B and C) an example of a sca...
Scheme 4: (A) Known biological activities related to sulfur-containing compounds; (B and C) an example of a s...
Scheme 5: (A) Known biological activities related to aminoindane derivatives; (B and C) an example of a scand...
Scheme 6: (A) Known biological activities related to norbornane derivatives; (B and C) an example of a scandi...
Scheme 7: (A) Known biological activities related to aniline derivatives; (B and C) an example of a titanium-...
Scheme 8: (A) Known biological activities related to cyclohexylamine derivatives; (B) an example of an intram...
Scheme 9: (A) Known biologically active benzophenone derivatives; (B and C) photocatalytic oxidation of benzy...
Scheme 10: (A) Known bioactive fluorine-containing compounds; (B and C) vanadium-mediated C(sp3)–H fluorinatio...
Scheme 11: (A) Known biologically active Lythraceae alkaloids; (B) synthesis of (±)-decinine (30).
Scheme 12: (A) Synthesis of (R)- and (S)-boehmeriasin (31); (B) synthesis of phenanthroindolizidines by vanadi...
Scheme 13: (A) Known bioactive BINOL derivatives; (B and C) vanadium-mediated oxidative coupling of 2-naphthol...
Scheme 14: (A) Known antiplasmodial imidazopyridazines; (B) practical synthesis of 41.
Scheme 15: (A) Gold-catalyzed drug-release mechanism using 2-alkynylbenzamides; (B and C) chromium-mediated al...
Scheme 16: (A) Examples of anti-inflammatory benzaldehyde derivatives; (B and C) chromium-mediated difunctiona...
Scheme 17: (A and B) Manganese-catalyzed chemoselective intramolecular C(sp3)–H amination; (C) late-stage modi...
Scheme 18: (A and B) Manganese-catalyzed C(sp3)–H amination; (C) late-stage modification of a leelamine deriva...
Scheme 19: (A) Known bioactive compounds containing substituted N-heterocycles; (B and C) manganese-catalyzed ...
Scheme 20: (A) Known indoles that present GPR40 full agonist activity; (B and C) manganese-catalyzed C–H alkyl...
Scheme 21: (A) Examples of known biaryl-containing drugs; (B and C) manganese-catalyzed C–H arylation through ...
Scheme 22: (A) Known zidovudine derivatives with potent anti-HIV properties; (B and C) manganese-catalyzed C–H...
Scheme 23: (A and B) Manganese-catalyzed C–H organic photo-electrosynthesis; (C) late-stage modification.
Scheme 24: (A) Example of a known antibacterial silylated dendrimer; (B and C) manganese-catalyzed C–H silylat...
Scheme 25: (A and B) Fe-based small molecule catalyst applied for selective aliphatic C–H oxidations; (C) late...
Scheme 26: (A) Examples of naturally occurring gracilioethers; (B) the first total synthesis of gracilioether ...
Scheme 27: (A and B) Selective aliphatic C–H oxidation of amino acids; (C) late-stage modification of proline-...
Scheme 28: (A) Examples of Illicium sesquiterpenes; (B) first chemical synthesis of (+)-pseudoanisatin (80) in...
Scheme 29: (A and B) Fe-catalyzed deuteration; (C) late-stage modification of pharmaceuticals.
Scheme 30: (A and B) Biomimetic Fe-catalyzed aerobic oxidation of methylarenes to benzaldehydes (PMHS, polymet...
Scheme 31: (A) Known tetrahydroquinolines with potential biological activities; (B and C) redox-selective Fe c...
Scheme 32: (A) Known drugs containing a benzofuran unit; (B and C) Fe/Cu-catalyzed tandem O-arylation to acces...
Scheme 33: (A) Known azaindolines that act as M4 muscarinic acetylcholine receptor agonists; (B and C) intramo...
Scheme 34: (A) Known indolinones with anticholinesterase activity; (B and C) oxidative C(sp3)–H cross coupling...
Scheme 35: (A and B) Cobalt-catalyzed C–H alkenylation of C-3-peptide-containing indoles; (C) derivatization b...
Scheme 36: (A) Cobalt-Cp*-catalyzed C–H methylation of known drugs; (B and C) scope of the o-methylated deriva...
Scheme 37: (A) Known lasalocid A analogues; (B and C) three-component cobalt-catalyzed C–H bond addition; (D) ...
Scheme 38: (A and B) Cobalt-catalyzed C(sp2)–H amidation of thiostrepton.
Scheme 39: (A) Known 4H-benzo[d][1,3]oxazin-4-one derivatives with hypolipidemic activity; (B and C) cobalt-ca...
Scheme 40: (A and B) Cobalt-catalyzed C–H arylation of pyrrole derivatives; (C) application for the synthesis ...
Scheme 41: (A) Known 2-phenoxypyridine derivatives with potent herbicidal activity; (B and C) cobalt-catalyzed...
Scheme 42: (A) Natural cinnamic acid derivatives; (B and C) cobalt-catalyzed C–H carboxylation of terminal alk...
Scheme 43: (A and B) Cobalt-catalyzed C–H borylation; (C) application to the synthesis of flurbiprofen.
Scheme 44: (A) Benzothiazoles known to present anticonvulsant activities; (B and C) cobalt/ruthenium-catalyzed...
Scheme 45: (A and B) Cobalt-catalyzed oxygenation of methylene groups towards ketone synthesis; (C) synthesis ...
Scheme 46: (A) Known anticancer tetralone derivatives; (B and C) cobalt-catalyzed C–H difluoroalkylation of ar...
Scheme 47: (A and B) Cobalt-catalyzed C–H thiolation; (C) application in the synthesis of quetiapine (153).
Scheme 48: (A) Known benzoxazole derivatives with anticancer, antifungal, and antibacterial activities; (B and...
Scheme 49: (A and B) Cobalt-catalyzed C–H carbonylation of naphthylamides; (C) BET inhibitors 158 and 159 tota...
Scheme 50: (A) Known bioactive pyrrolo[1,2-a]quinoxalin-4(5H)-one derivatives; (B and C) cobalt-catalyzed C–H ...
Scheme 51: (A) Known antibacterial cyclic sulfonamides; (B and C) cobalt-catalyzed C–H amination of propargyli...
Scheme 52: (A and B) Cobalt-catalyzed intramolecular 1,5-C(sp3)–H amination; (C) late-stage functionalization ...
Scheme 53: (A and B) Cobalt-catalyzed C–H/C–H cross-coupling between benzamides and oximes; (C) late-state syn...
Scheme 54: (A) Known anticancer natural isoquinoline derivatives; (B and C) cobalt-catalyzed C(sp2)–H annulati...
Scheme 55: (A) Enantioselective intramolecular nickel-catalyzed C–H activation; (B) bioactive obtained motifs;...
Scheme 56: (A and B) Nickel-catalyzed α-C(sp3)–H arylation of ketones; (C) application of the method using kno...
Scheme 57: (A and B) Nickel-catalyzed C(sp3)–H acylation of pyrrolidine derivatives; (C) exploring the use of ...
Scheme 58: (A) Nickel-catalyzed C(sp3)–H arylation of dioxolane; (B) library of products obtained from biologi...
Scheme 59: (A) Intramolecular enantioselective nickel-catalyzed C–H cycloalkylation; (B) product examples, inc...
Scheme 60: (A and B) Nickel-catalyzed C–H deoxy-arylation of azole derivatives; (C) late-stage functionalizati...
Scheme 61: (A and B) Nickel-catalyzed decarbonylative C–H arylation of azole derivatives; (C) application of t...
Scheme 62: (A and B) Another important example of nickel-catalyzed C–H arylation of azole derivatives; (C) app...
Scheme 63: (A and B) Another notable example of a nickel-catalyzed C–H arylation of azole derivatives; (C) lat...
Scheme 64: (A and B) Nickel-based metalorganic framework (MOF-74-Ni)-catalyzed C–H arylation of azole derivati...
Scheme 65: (A) Known commercially available benzothiophene-based drugs; (B and C) nickel-catalyzed C–H arylati...
Scheme 66: (A) Known natural tetrahydrofuran-containing substances; (B and C) nickel-catalyzed photoredox C(sp3...
Scheme 67: (A and B) Another notable example of a nickel-catalyzed photoredox C(sp3)–H alkylation/arylation; (...
Scheme 68: (A) Electrochemical/nickel-catalyzed C–H alkoxylation; (B) achieved scope, including three using na...
Scheme 69: (A) Enantioselective photoredox/nickel catalyzed C(sp3)–H arylation; (B) achieved scope, including ...
Scheme 70: (A) Known commercially available trifluoromethylated drugs; (B and C) nickel-catalyzed C–H trifluor...
Scheme 71: (A and B) Stereoselective nickel-catalyzed C–H difluoroalkylation; (C) late-stage functionalization...
Scheme 72: (A) Cu-mediated ortho-amination of oxalamides; (B) achieved scope, including derivatives obtained f...
Scheme 73: (A) Electro-oxidative copper-mediated amination of 8-aminoquinoline-derived amides; (B) achieved sc...
Scheme 74: (A and B) Cu(I)-mediated C–H amination with oximes; (C) derivatization using telmisartan (241) as s...
Scheme 75: (A and B) Cu-mediated amination of aryl amides using ammonia; (C) late-stage modification of proben...
Scheme 76: (A and B) Synthesis of purine nucleoside analogues using copper-mediated C(sp2)–H activation.
Scheme 77: (A) Copper-mediated annulation of acrylamide; (B) achieved scope, including the synthesis of the co...
Scheme 78: (A) Known bioactive compounds containing a naphthyl aryl ether motif; (B and C) copper-mediated eth...
Scheme 79: (A and B) Cu-mediated alkylation of N-oxide-heteroarenes; (C) late-stage modification.
Scheme 80: (A) Cu-mediated cross-dehydrogenative coupling of polyfluoroarenes and alkanes; (B) scope from know...
Scheme 81: (A) Known anticancer acrylonitrile compounds; (B and C) Copper-mediated cyanation of unactivated al...
Scheme 82: (A) Cu-mediated radiofluorination of 8-aminoquinoline-derived aryl amides; (B) achieved scope, incl...
Scheme 83: (A) Examples of natural β-carbolines; (B and C) an example of a zinc-catalyzed C–H functionalizatio...
Scheme 84: (A) Examples of anticancer α-aminophosphonic acid derivatives; (B and C) an example of a zinc-catal...
Beilstein J. Org. Chem. 2021, 17, 1727–1732, doi:10.3762/bjoc.17.121
Graphical Abstract
Scheme 1: Photocatalyzed aerobic oxidation of aromatic alcohols.
Scheme 2: Substrate scope. Reaction conditions as given in Table 1 (entry 1). Yields are isolated yields, average of...
Scheme 3: Selective oxidation of 3-bromobenzyl alcohol in the presence of 3-phenylpropanol. Compound 1af was ...
Figure 1: Mechanistic studies. (A): UV–vis spectra of the CeIV(OBn)Cln complex in CH3CN under blue light irra...
Beilstein J. Org. Chem. 2020, 16, 3093–3103, doi:10.3762/bjoc.16.259
Graphical Abstract
Scheme 1: Benzylic addition of aldehydes to azaarenes using different catalysts.
Scheme 2: Synthesis of azaarene derivatives from different precursors.
Scheme 3: Our work: catalyst- and solvent-free benzylic addition of aldehydes to azaarenes.
Scheme 4: Large-scale experiments for the synthesis of 2-(6-methylpyridin-2-yl)-1-(4-nitrophenyl)ethan-1-ol (...
Scheme 5: Plausible mechanism for the formation of 2-(6-methylpyridin-2-yl)-1-(4-nitrophenyl)ethan-1-ol (3a) ...
Beilstein J. Org. Chem. 2020, 16, 2607–2622, doi:10.3762/bjoc.16.212
Graphical Abstract
Scheme 1: General scheme of the suggested synthesis of nucleosides employing the enzymatic phosphorolysis of ...
Figure 1: Phosphorolysis (5.0 mM K-phosphate buffer, pH 7.0; 23 °C) of Ara-U and thymidine (Thd) catalyzed by...
Scheme 2: Transarabinosylation of O6-methylguanine (OMG) employing Ara-U as a donor of the Ara-1Pi (1:1.5 mol...
Figure 2: Optimized conditions of phosphorolysis of Ara-U: 0.20 mmol of Ara-U in distilled water (30 mL) cont...
Scheme 3: Synthesis of nelarabine with intermediate preparation of crude Ara-1Pi.
Scheme 4: Synthesis of kinetin riboside with intermediate preparation of crude Rib-1Pi.
Beilstein J. Org. Chem. 2020, 16, 2484–2504, doi:10.3762/bjoc.16.202
Graphical Abstract
Figure 1: The momentum transport affects the mass transfer and the light field. All transport phenomena need ...
Figure 2: Common photomicroreactor designs: (a) Straight channel, (b) serpentine channel, (c) square serpenti...
Figure 3: Benchmarked photoreactors: (a) Microcapillaries in parallel, (b) microcapillaries in series, (c) fl...
Figure 4: Photochemical reactions that are detailed in Table 1.
Figure 5: Structured reactors designed for enhancing the mass transfer: (a) Packed bed photoreactor, (b) mono...
Figure 6: Comparison of the LED board designs of photomicroreactors: (a) CC array design, (b) MC array design...
Figure 7: Illustration of the light scattering phenomenon inside a photocatalytic flow reactor.
Figure 8: Efficiency of the absorption process in scattering situations with respect to pure absorption situa...
Figure 9: Different types of distributors: (a) Traditional or consecutive manifold, (b) bifurcation unit dist...
Beilstein J. Org. Chem. 2020, 16, 1924–1935, doi:10.3762/bjoc.16.159
Graphical Abstract
Scheme 1: Synthesis of NHC-supported catalysts.
Scheme 2: Negishi benchmark reaction.
Figure 1: Negishi reaction catalyzed by immobilized NHC–Pd complexes. Conditions: methyl 4-bromobenzoate (0.2...
Scheme 3: Synthesis of immobilized NHC–Pd–RuPhos.
Figure 2: Negishi model reaction between 5 and 6 under flow conditions catalyzed by 4b. V = 0.535 mL, 363 mg ...
Figure 3: Negishi model reaction under flow conditions catalyzed by 8a. V = 2.9 mL, 1.25 g of catalyst, resid...
Figure 4: Negishi reaction between 5 and 6 catalyzed by 8a in the presence of SILLPs. a) Yield (%) vs time fo...
Figure 5: TEM images of the polymers after the Negishi reaction between 5 and 6. a) 8a, bar scale 20 nm, PdNP...
Scheme 4: Pd species immobilized onto SILLPs. i) 1 g SILLP 10, 100 mg PdCl2 in milli-Q® water (100 mL 1% HCl,...
Figure 6: Negishi reaction between 5 and 6 catalyzed by 11. 1 equiv methyl 4-bromobenzoate (6, 0.25 mmol), 2 ...
Figure 7: Negishi reaction between 5 and 6 under flow conditions catalyzed by 8a in the presence of a scaveng...
Figure 8: Effect of the structure of the SILLP scavenger for the Negishi reaction between 5 and 6 under flow ...
Figure 9: TEM images of the polymer after the Negishi reaction between 5 and 6 under flow conditions. a) 8a + ...
Beilstein J. Org. Chem. 2020, 16, 1662–1682, doi:10.3762/bjoc.16.138
Graphical Abstract
Scheme 1: Schematic representation of the Pauson–Khand reaction.
Scheme 2: Substrates included in this review.
Scheme 3: Commonly accepted mechanism for the Pauson–Khand reaction.
Scheme 4: Regioselectivity of the PKR.
Scheme 5: Variability at the acetylenic and olefinic counterpart.
Scheme 6: Pauson–Khand reaction of fluoroolefinic enynes reported by the group of Ishizaki [46].
Scheme 7: PKR of enynes bearing fluorinated groups on the alkynyl moiety, reported by the group of Ishizaki [46]....
Scheme 8: Intramolecular PKR of 1,7-enynes reported by the group of Billard [47].
Scheme 9: Intramolecular PKR of 1,7-enynes reported by the group of Billard [48].
Scheme 10: Intramolecular PKR of 1,7-enynes by the group of Bonnet-Delpon [49]. Reaction conditions: i) Co(CO)8 (1...
Scheme 11: Intramolecular PKR of 1,6-enynes reported by the group of Ichikawa [50].
Scheme 12: Intramolecular Rh(I)-catalyzed PKR reported by the group of Hammond [52].
Scheme 13: Intramolecular PKR of allenynes reported by the group of Osipov [53].
Scheme 14: Intramolecular PKR of 1,7-enynes reported by the group of Osipov [53].
Scheme 15: Intramolecular PKR of fluorine-containing 1,6-enynes reported by the Konno group [54].
Scheme 16: Diastereoselective PKR with enantioenriched fluorinated enynes 34 [55].
Scheme 17: Intramolecular PKR reported by the group of Martinez-Solorio [56].
Scheme 18: Fluorine substitution at the olefinic counterpart.
Scheme 19: Synthesis of fluorinated enynes 37 [59].
Scheme 20: Fluorine-containing substrates in PKR [59].
Scheme 21: Pauson Khand reaction for fluorinated enynes by the Fustero group: scope and limitations [59].
Scheme 22: Synthesis of chloro and bromo analogues [59].
Scheme 23: Dimerization pathway [59].
Scheme 24: Synthesis of fluorine-containing N-tethered 1,7-enynes [61].
Scheme 25: Intramolecular PKR of chiral N-tethered fluorinated 1,7-enynes [61].
Scheme 26: Examples of further modifications to the Pauson−Khand adducts [61].
Scheme 27: Asymmetric synthesis the fluorinated enynes 53.
Scheme 28: Intramolecular PKR of chiral N-tethered 1,7-enynes 53 [64].
Scheme 29: Intramolecular PKR of chiral N-tethered 1,7-enyne bearing a vinyl fluoride [64].
Scheme 30: Catalytic intramolecular PKR of chiral N-tethered 1,7-enynes [64].
Scheme 31: Model fluorinated alkynes used by Riera and Fustero [70].
Scheme 32: PKR with norbornadiene and fluorinated alkynes 58 [71].
Scheme 33: Nucleophilic addition/detrifluoromethylation and retro Diels-Alder reactions [70].
Scheme 34: Tentative mechanism for the nucleophilic addition/retro-aldol reaction sequence.
Scheme 35: Catalytic PKR with norbornadiene [70].
Scheme 36: Scope of the PKR of trifluoromethylalkynes with norbornadiene [72].
Scheme 37: DBU-mediated detrifluoromethylation [72].
Scheme 38: A simple route to enone 67, a common intermediate in the total synthesis of α-cuparenone.
Scheme 39: Effect of the olefin partner in the regioselectivity of the PKR with trifluoromethyl alkynes [79].
Scheme 40: Intermolecular PKR of trifluoromethylalkynes with 2-norbornene reported by the group of Konno [54].
Scheme 41: Intermolecular PKR of diarylalkynes with 2-norbornene reported by the group of Helaja [80].
Scheme 42: Intermolecular PKR reported by León and Fernández [81].
Scheme 43: PKR reported with cyclopropene 73 [82].
Beilstein J. Org. Chem. 2020, 16, 982–988, doi:10.3762/bjoc.16.87
Graphical Abstract
Scheme 1: One-day workflow for fragment-based library generation. QC: Quality control. MPLC: Medium-pressure ...
Figure 1: Top: high-power blue LED photoreactors. Bottom, from left to right: photoreactor OFF, ON, and ON th...
Figure 2: TLC–MS equipment: analysis of 5 reactions in 5 minutes.
Figure 3: Pre-QC validation by 60 MHz benchtop NMR.
Scheme 2: Scope of the fragment-based library generation: BCP-amines and azetidines. See Supporting Information File 1 for experimental de...
Scheme 3: Scope of the fragment-based library generation: pyrrolidines, piperidines and morpholines. See Supporting Information File 1 for...
Beilstein J. Org. Chem. 2020, 16, 645–656, doi:10.3762/bjoc.16.61
Graphical Abstract
Figure 1: Rhodium-catalyzed reductive carbonylation of iodobenzene with CO and H2 to afford benzaldehyde. a) ...
Scheme 1: Scaled-up experiment of the reductive carbonylation of iodobenzene to benzaldehyde under the optimi...
Scheme 2: Catalytic species participating in the catalytic process.
Scheme 3: Substrate scope for the Rh-catalyzed reductive carbonylation of aryl iodides using CO and H2. React...
Scheme 4: Isotope-labeling experiments.
Scheme 5: Proposed reaction mechanism for the Rh-catalyzed reductive carbonylation of aryl iodides using CO a...