Search for "methoxylation" in Full Text gives 21 result(s) in Beilstein Journal of Organic Chemistry.
Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85
Graphical Abstract
Figure 1: Biologically active cinnamic acid derivatives.
Scheme 1: General synthetic strategies for cinnamic acid derivatizations.
Scheme 2: Cinnamic acid coupling via isobutyl anhydride formation.
Scheme 3: Amidation reaction via O/N-pivaloyl activation.
Scheme 4: Cinnamic acid amidation using TCCA/PPh3 reagent.
Scheme 5: Cinnamic acid amidation using triazine-based reagents.
Scheme 6: Cinnamic acid amidation using continuous flow mechanochemistry.
Scheme 7: Cinnamic acid amidation using COMU as coupling reagent.
Scheme 8: Cinnamic acid amidation using allenone coupling reagent.
Scheme 9: Cinnamic acid amidation using 4-acetamidophenyl triflimide as reagent.
Scheme 10: Cinnamic acid amidation using methyltrimethoxysilane (MTM).
Scheme 11: Cinnamic acid amidation utilizing amine–borane reagent.
Scheme 12: Cinnamic acid amidation using TCCA/PPh3 reagent.
Scheme 13: Cinnamic acid amidation using PPh3/I2 reagent.
Scheme 14: Cinnamic acid amidation using PCl3 reagent.
Scheme 15: Cinnamic acid amidation utilizing pentafluoropyridine (PFP) as reagent.
Scheme 16: Cinnamic acid amidation using hypervalent iodine(III).
Scheme 17: Mechanochemical amidation using 1,1,2,2-tetrafluoroethyl-N,N-dimethylamine (TFEDMA) reagent.
Scheme 18: Methyl ester preparation using tris(2,4,6-trimethoxyphenyl)phosphine (TMPP).
Scheme 19: N-Trifluoromethyl amide preparation using isothiocyanate and AgF.
Scheme 20: POCl3-mediated amide coupling of carboxylic acid and DMF.
Scheme 21: O-Alkylation of cinnamic acid using alkylating agents.
Scheme 22: Glycoside preparation via Mitsunobu reaction.
Scheme 23: O/N-Acylation via rearrangement reactions.
Scheme 24: Amidation reactions using sulfur-based alkylating agents.
Scheme 25: Amidation reaction catalyzed by Pd0 via C–N cleavage.
Scheme 26: Amidation reaction catalyzed by CuCl/PPh3.
Scheme 27: Cu(II) triflate-catalyzed N-difluoroethylimide synthesis.
Scheme 28: Cu/Selectfluor-catalyzed transamidation reaction.
Scheme 29: CuO–CaCO3-catalyzed amidation reaction.
Scheme 30: Ni-catalyzed reductive amidation.
Scheme 31: Lewis acidic transition-metal-catalyzed O/N-acylations.
Scheme 32: Visible-light-promoted amidation of cinnamic acid.
Scheme 33: Sunlight/LED-promoted amidation of cinnamic acid.
Scheme 34: Organophotocatalyst-promoted N–O cleavage of Weinreb amides to synthesize primary amides.
Scheme 35: Cinnamamide synthesis through [Ir] photocatalyst-promoted C–N-bond cleavage of tertiary amines.
Scheme 36: Blue LED-promoted FeCl3-catalyzed reductive transamidation.
Scheme 37: FPyr/TCT-catalyzed amidation of cinnamic acid derivative 121.
Scheme 38: Cs2CO3/DMAP-mediated esterification.
Scheme 39: HBTM organocatalyzed atroposelective N-acylation.
Scheme 40: BH3-catalyzed N-acylation reactions.
Scheme 41: Borane-catalyzed N-acylation reactions.
Scheme 42: Catalytic N-acylation reactions via H/F bonding activation.
Scheme 43: Brønsted base-catalyzed synthesis of cinnamic acid esters.
Scheme 44: DABCO/Fe3O4-catalyzed N-methyl amidation of cinnamic acid 122.
Scheme 45: Catalytic oxidation reactions of acylating agents.
Scheme 46: Preparation of cinnamamide-substituted benzocyclooctene using I(I)/I(III) catalysis.
Scheme 47: Pd-colloids-catalyzed oxidative esterification of cinnamyl alcohol.
Scheme 48: Graphene-supported Pd/Au alloy-catalyzed oxidative esterification via hemiacetal intermediate.
Scheme 49: Au-supported on A) carbon nanotubes (CNT) and B) on porous boron nitride (pBN) as catalyst for the ...
Scheme 50: Cr-based catalyzed oxidative esterification of cinnamyl alcohols with H2O2 as the oxidant.
Scheme 51: Co-based catalysts used for oxidative esterification of cinnamyl alcohol.
Scheme 52: Iron (A) and copper (B)-catalyzed oxidative esterification of cinnamaldehyde.
Scheme 53: NiHPMA-catalyzed oxidative esterification of cinnamaldehyde.
Scheme 54: Synthesis of cinammic acid esters through NHC-catalyzed oxidative esterification via intermolecular...
Scheme 55: Redox-active NHC-catalyzed esterification via intramolecular oxidation.
Scheme 56: Electrochemical conversion of cinnamaldehyde to methyl cinnamate.
Scheme 57: Bu4NI/TBHP-catalyzed synthesis of bisamides from cinnamalaldehyde N-tosylhydrazone.
Scheme 58: Zn/NC-950-catalyzed oxidative esterification of ketone 182.
Scheme 59: Ru-catalyzed oxidative carboxylation of terminal alkenes.
Scheme 60: Direct carboxylation of alkenes using CO2.
Scheme 61: Carboxylation of alkenylboronic acid/ester.
Scheme 62: Carboxylation of gem-difluoroalkenes with CO2.
Scheme 63: Photoredox-catalyzed carboxylation of difluoroalkenes.
Scheme 64: Ru-catalyzed carboxylation of alkenyl halide.
Scheme 65: Carboxylation of alkenyl halides under flow conditions.
Scheme 66: Cinnamic acid ester syntheses through carboxylation of alkenyl sulfides/sulfones.
Scheme 67: Cinnamic acid derivatives synthesis through a Ag-catalyzed decarboxylative cross-coupling proceedin...
Scheme 68: Pd-catalyzed alkyne hydrocarbonylation.
Scheme 69: Fe-catalyzed alkyne hydrocarbonylation.
Scheme 70: Alkyne hydrocarboxylation using CO2.
Scheme 71: Alkyne hydrocarboxylation using HCO2H as CO surrogate.
Scheme 72: Co/AlMe3-catalyzed alkyne hydrocarboxylation using DMF.
Scheme 73: Au-catalyzed oxidation of Au–allenylidenes.
Scheme 74: Pd-catalyzed C–C-bond activation of cyclopropenones to synthesize unsaturated esters and amides.
Scheme 75: Ag-catalyzed C–C-bond activation of diphenylcyclopropenone.
Scheme 76: Cu-catalyzed C–C bond activation of diphenylcyclopropenone.
Scheme 77: PPh3-catalyzed C–C-bond activation of diphenylcyclopropenone.
Scheme 78: Catalyst-free C–C-bond activation of diphenylcyclopropenone.
Scheme 79: Cu-catalyzed dioxolane cleavage.
Scheme 80: Multicomponent coupling reactions.
Scheme 81: Pd-catalyzed partial hydrogenation of electrophilic alkynes.
Scheme 82: Nickel and cobalt as earth-abundant transition metals used as catalysts for the partial hydrogenati...
Scheme 83: Metal-free-catalyzed partial hydrogenation of conjugated alkynes.
Scheme 84: Horner–Wadsworth–Emmons reaction between triethyl 2-fluoro-2-phosphonoacetate and aldehydes with ei...
Scheme 85: Preparation of E/Z-cinnamates using thiouronium ylides.
Scheme 86: Transition-metal-catalyzed ylide reactions.
Scheme 87: Redox-driven ylide reactions.
Scheme 88: Noble transition-metal-catalyzed olefination via carbenoid species.
Scheme 89: TrBF4-catalyzed olefination via carbene species.
Scheme 90: Grubbs catalyst (cat 7)/photocatalyst-mediated metathesis reactions.
Scheme 91: Elemental I2-catalyzed carbonyl-olefin metathesis.
Scheme 92: Cu-photocatalyzed E-to-Z isomerization of cinnamic acid derivatives.
Scheme 93: Ni-catalyzed E-to-Z isomerization.
Scheme 94: Dehydration of β-hydroxy esters via an E1cB mechanism to access (E)-cinnamic acid esters.
Scheme 95: Domino ring-opening reaction induced by a base.
Scheme 96: Dehydroamination of α-aminoester derivatives.
Scheme 97: Accessing methyl cinnamate (44) via metal-free deamination or decarboxylation.
Scheme 98: The core–shell magnetic nanosupport-catalyzed condensation reaction.
Scheme 99: Accessing cinnamic acid derivatives from acetic acid esters/amides through α-olefination.
Scheme 100: Accessing cinnamic acid derivatives via acceptorless α,β-dehydrogenation.
Scheme 101: Cu-catalyzed formal [3 + 2] cycloaddition.
Scheme 102: Pd-catalyzed C–C bond formation via 1,4-Pd-shift.
Scheme 103: NHC-catalyzed Rauhut–Currier reactions.
Scheme 104: Heck-type reaction for Cα arylation.
Scheme 105: Cu-catalyzed trifluoromethylation of cinnamamide.
Scheme 106: Ru-catalyzed alkenylation of arenes using directing groups.
Scheme 107: Earth-abundant transition-metal-catalyzed hydroarylation of α,β-alkynyl ester 374.
Scheme 108: Precious transition-metal-catalyzed β-arylation of cinnamic acid amide/ester.
Scheme 109: Pd-catalyzed β-amination of cinnamamide.
Scheme 110: S8-mediated β-amination of methyl cinnamate (44).
Scheme 111: Pd-catalyzed cross-coupling reaction of alkynyl esters with phenylsilanes.
Scheme 112: Pd-catalyzed β-cyanation of alkynyl amide/ester.
Scheme 113: Au-catalyzed β-amination of alkynyl ester 374.
Scheme 114: Metal-free-catalyzed Cβ-functionalizations of alkynyl esters.
Scheme 115: Heck-type reactions.
Scheme 116: Mizoroki–Heck coupling reactions using unconventional functionalized arenes.
Scheme 117: Functional group-directed Mizoroki–Heck coupling reactions.
Scheme 118: Pd nanoparticles-catalyzed Mizoroki–Heck coupling reactions.
Scheme 119: Catellani-type reactions to access methyl cinnamate with multifunctionalized arene.
Scheme 120: Multicomponent coupling reactions.
Scheme 121: Single atom Pt-catalyzed Heck coupling reaction.
Scheme 122: Earth-abundant transition metal-catalyzed Heck coupling reactions.
Scheme 123: Polymer-coated earth-abundant transition metals-catalyzed Heck coupling reactions.
Scheme 124: Earth-abundant transition-metal-based nanoparticles as catalysts for Heck coupling reactions.
Scheme 125: CN- and Si-based directing groups to access o-selective cinnamic acid derivatives.
Scheme 126: Amide-based directing group to access o-selective cinnamic acid derivatives.
Scheme 127: Carbonyl-based directing group to access o-selective cinnamic acid derivatives.
Scheme 128: Stereoselective preparation of atropisomers via o-selective C(sp2)–H functionalization.
Scheme 129: meta-Selective C(sp2)–H functionalization using directing group-tethered arenes.
Scheme 130: para-Selective C(sp2)–H functionalization using directing group-tethered arenes.
Scheme 131: Non-directed C(sp2)–H functionalization via electrooxidative Fujiwara–Moritani reaction.
Scheme 132: Interconversion of functional groups attached to cinnamic acid.
Scheme 133: meta-Selective C(sp2)–H functionalization of cinnamate ester.
Scheme 134: C(sp2)–F arylation using Grignard reagents.
Scheme 135: Truce–Smiles rearrangement of N-aryl metacrylamides.
Scheme 136: Phosphine-catalyzed cyclization of γ-vinyl allenoate with enamino esters.
Beilstein J. Org. Chem. 2024, 20, 1746–1757, doi:10.3762/bjoc.20.153
Graphical Abstract
Scheme 1: Formation of phenoxonium cation in the anodic oxidation of phenol performed under neutral or weakly...
Scheme 2: Anodic oxidation reported by Swenton et al. [37].
Figure 1: Cyclic voltammograms of PAPs first scan at 0.1 V/s in 0.1 M [NBu4] [PF6] in MeCN and UV–vis spectra...
Scheme 3: Proposed mechanism for the formation of p-dimethoxy acetals in the anodic oxidation of 1b and 3b.
Figure 2: Resonance structures of the phenoxonium cation formed from 2-chrysenol (3a).
Beilstein J. Org. Chem. 2024, 20, 243–253, doi:10.3762/bjoc.20.24
Graphical Abstract
Scheme 1: Comparison of basicity (in water scale) and synthetic availability of quinoline-type azaarenes and ...
Figure 1: Suggested amination products 6 and two resonance forms of dianion 7.
Figure 2: Targeted dipyridoacenaphthylene 8.
Scheme 2: Formation of complex 9 and its slow hydrolytic degradation into protic salt 5·HCl.
Figure 3: Molecular and crystal structure of salt 5·HCl·2H2O is strongly dominated by severe H-bonding (blue ...
Figure 4: Selected images of the supramolecular organization of two molecules of base 5 held by 4,6-dichloror...
Figure 5: Fragment of the crystal packing of neutral dipyridoacenaphthene 5 showing self-association via mult...
Scheme 3: Dinitration of compound 5 and the initially assumed admixture 11.
Scheme 4: Mononitration of compound 5.
Figure 6: Structure of dinitroacenaphthylene 12.
Scheme 5: Dehydrogenation of compounds 10 and 11.
Scheme 6: Nucleophilic methoxylation of compounds 10(12).
Figure 7: Basicity of key compounds in acetonitrile.
Scheme 7: Electrophilic bromination of compound 5.
Scheme 8: tele-Elimination upon interaction of dibromide 15 with pyrrolidine.
Scheme 9: Interaction of dibromide 15 with anionic bases.
Beilstein J. Org. Chem. 2021, 17, 343–378, doi:10.3762/bjoc.17.32
Graphical Abstract
Figure 1: Stabilizing interaction in the CF3CH2+ carbenium ion (top) and structure of the first observable fl...
Scheme 1: Isodesmic equations accounting for the destabilizing effect of the CF3 group. ΔE in kcal⋅mol−1, cal...
Scheme 2: Stabilizing effect of fluorine atoms by resonance electron donation in carbenium ions (δ in ppm).
Scheme 3: Direct in situ NMR observation of α-(trifluoromethyl)carbenium ion or protonated alcohols. Δδ = δ19...
Scheme 4: Reported 13C NMR chemical shifts for the α-(trifluoromethyl)carbenium ion 10c (δ in ppm).
Scheme 5: Direct NMR observation of α-(trifluoromethyl)carbenium ions in situ (δ in ppm).
Scheme 6: Illustration of the ion pair solvolysis mechanism for sulfonate 13f. YOH = solvent.
Figure 2: Solvolysis rate for 13a–i and 17.
Figure 3: Structures of allyl triflates 18 and 19 and allyl brosylate 20. Bs = p-BrC6H4SO2.
Figure 4: Structure of tosylate derivatives 21.
Figure 5: a) Structure of triflate derivatives 22. b) Stereochemistry outcomes of the reaction starting from (...
Scheme 7: Solvolysis reaction of naphthalene and anthracenyl derivatives 26 and 29.
Figure 6: Structure of bisarylated derivatives 34.
Figure 7: Structure of bisarylated derivatives 36.
Scheme 8: Reactivity of 9c in the presence of a Brønsted acid.
Scheme 9: Cationic electrocyclization of 38a–c under strongly acidic conditions.
Scheme 10: Brønsted acid-catalyzed synthesis of indenes 42 and indanes 43.
Scheme 11: Reactivity of sulfurane 44 in triflic acid.
Scheme 12: Solvolysis of triflate 45f in alcoholic solvents.
Scheme 13: Synthesis of labeled 18O-52.
Scheme 14: Reactivity of sulfurane 53 in triflic acid.
Figure 8: Structure of tosylates 56 and 21f.
Scheme 15: Resonance forms in benzylic carbenium ions.
Figure 9: Structure of pyrrole derivatives 58 and 59.
Scheme 16: Resonance structure 60↔60’.
Scheme 17: Ga(OTf)3-catalyzed synthesis of 3,3’- and 3,6’-bis(indolyl)methane from trifluoromethylated 3-indol...
Scheme 18: Proposed reaction mechanism.
Scheme 19: Metal-free 1,2-phosphorylation of 3-indolylmethanols.
Scheme 20: Superacid-mediated arylation of thiophene derivatives.
Scheme 21: In situ mechanistic NMR investigations.
Scheme 22: Proposed mechanisms for the prenyltransferase-catalyzed condensation.
Scheme 23: Influence of a CF3 group on the allylic SN1- and SN2-mechanism-based reactions.
Scheme 24: Influence of the CF3 group on the condensation reaction.
Scheme 25: Solvolysis of 90 in TFE.
Scheme 26: Solvolysis of allyl triflates 94 and 97 and isomerization attempt of 96.
Scheme 27: Proposed mechanism for the formation of 95.
Scheme 28: Formation of α-(trifluoromethyl)allylcarbenium ion 100 in a superacid.
Scheme 29: Lewis acid activation of CF3-substituted allylic alcohols.
Scheme 30: Bimetallic-cluster-stabilized α-(trifluoromethyl)carbenium ions.
Scheme 31: Reactivity of cluster-stabilized α-(trifluoromethyl)carbenium ions.
Scheme 32: α-(Trifluoromethyl)propargylium ion 122↔122’ generated from silyl ether 120 in a superacid.
Scheme 33: Formation of α-(trifluoromethyl)propargylium ions from CF3-substituted propargyl alcohols.
Scheme 34: Direct NMR observation of the protonation of some trifluoromethyl ketones in situ and the correspon...
Scheme 35: Selected resonance forms in protonated fluoroketone derivatives.
Scheme 36: Acid-catalyzed Friedel–Crafts reactions of trifluoromethyl ketones 143a,b and 147a–c.
Scheme 37: Enantioselective hydroarylation of CF3-substituted ketones.
Scheme 38: Acid-catalyzed arylation of ketones 152a–c.
Scheme 39: Reactivity of 156 in a superacid.
Scheme 40: Reactivity of α-CF3-substituted heteroaromatic ketones and alcohols as well as 1,3-diketones.
Scheme 41: Reactivity of 168 with benzene in the presence of a Lewis or Brønsted acid.
Scheme 42: Acid-catalyzed three-component asymmetric reaction.
Scheme 43: Anodic oxidation of amines 178a–c and proposed mechanism.
Scheme 44: Reactivity of 179b in the presence of a strong Lewis acid.
Scheme 45: Trifluoromethylated derivatives as precursors of trifluoromethylated iminium ions.
Scheme 46: Mannich reaction with trifluoromethylated hemiaminal 189.
Scheme 47: Suitable nucleophiles reacting with 192 after Lewis acid activation.
Scheme 48: Strecker reaction involving the trifluoromethylated iminium ion 187.
Scheme 49: Reactivity of 199 toward nucleophiles.
Scheme 50: Reactivity of 204a with benzene in the presence of a Lewis acid.
Scheme 51: Reactivity of α-(trifluoromethyl)-α-chloro sulfides in the presence of strong Lewis acids.
Scheme 52: Anodic oxidation of sulfides 213a–h and Pummerer rearrangement.
Scheme 53: Mechanism for the electrochemical oxidation of the sulfide 213a.
Scheme 54: Reactivity of (trifluoromethyl)diazomethane (217a) in HSO3F.
Figure 10: a) Structure of diazoalkanes 217a–c and b) rate-limiting steps of their decomposition.
Scheme 55: Deamination reaction of racemic 221 and enantioenriched (S)-221.
Scheme 56: Deamination reaction of labeled 221-d2. Elimination products were formed in this reaction, the yiel...
Scheme 57: Deamination reaction of 225-d2. Elimination products were also formed in this reaction in undetermi...
Scheme 58: Formation of 229 from 228 via 1,2-H-shift.
Scheme 59: Deamination reaction of 230. Elimination products were formed in this reaction, the yield of which ...
Scheme 60: Deamination of several diazonium ions. Elimination products were formed in these reactions, the yie...
Scheme 61: Solvolysis reaction mechanism of alkyl tosylates.
Scheme 62: Solvolysis outcome for the tosylates 248 and 249 in HSO3FSbF5.
Figure 11: Solvolysis rate of 248, 249, 252, and 253 in 91% H2SO4.
Scheme 63: Illustration of the reaction pathways. TsCl, pyridine, −5 °C (A); 98% H2SO4, 30 °C (B); 98% H2SO4, ...
Scheme 64: Proposed solvolysis mechanism for the aliphatic tosylate 248.
Scheme 65: Solvolysis of the derivatives 259 and 260.
Scheme 66: Solvolysis of triflate 261. SOH = solvent.
Scheme 67: Intramolecular Friedel–Crafts alkylations upon the solvolysis of triflates 264 and 267.
Scheme 68: α-CF3-enhanced γ-silyl elimination of cyclobutyltosylates 270a,b.
Scheme 69: γ-Silyl elimination in the synthesis of a large variety of CF3-substituted cyclopropanes. Pf = pent...
Scheme 70: Synthetic pathways to 281. aNMR yields.
Scheme 71: The cyclopropyl-substituted homoallylcyclobutylcarbenium ion manifold.
Scheme 72: Reactivity of CF3-substituted cyclopropylcarbinyl derivatives 287a–c. LG = leaving group.
Scheme 73: Reactivity of CF3-substituted cyclopropylcarbinyl derivatives 291a–c.
Scheme 74: Superacid-promoted dimerization or TFP.
Scheme 75: Reactivity of TFP in a superacid.
Scheme 76: gem-Difluorination of α-fluoroalkyl styrenes via the formation of a “hidden” α-RF-substituted carbe...
Scheme 77: Solvolysis of CF3-substituted pentyne 307.
Scheme 78: Photochemical rearrangement of 313.
Figure 12: Structure of 2-norbornylcarbenium ion 318 and argued model for the stabilization of this cation.
Figure 13: Structures and solvolysis rate (TFE, 25 °C) of the sulfonates 319–321. Mos = p-MeOC6H4SO2.
Scheme 79: Mechanism for the solvolysis of 323. SOH = solvent.
Scheme 80: Products formed by the hydrolysis of 328.
Scheme 81: Proposed carbenium ion intermediates in an equilibrium during the solvolysis of tosylates 328, 333,...
Beilstein J. Org. Chem. 2020, 16, 451–481, doi:10.3762/bjoc.16.42
Graphical Abstract
Scheme 1: [Cu(I)(dap)2]Cl-catalyzed ATRA reaction under green light irradiation.
Scheme 2: Photocatalytic allylation of α-haloketones.
Scheme 3: [Cu(I)(dap)2]Cl-photocatalyzed chlorosulfonylation and chlorotrifluoromethylation of alkenes.
Scheme 4: Photocatalytic perfluoroalkylchlorination of electron-deficient alkenes using the Sauvage catalyst.
Scheme 5: Photocatalytic synthesis of fluorinated sultones.
Scheme 6: Photocatalyzed haloperfluoroalkylation of alkenes and alkynes.
Scheme 7: Chlorosulfonylation of alkenes catalyzed by [Cu(I)(dap)2]Cl. aNo Na2CO3 was added. b1 equiv of Na2CO...
Scheme 8: Copper-photocatalyzed reductive allylation of diaryliodonium salts.
Scheme 9: Copper-photocatalyzed azidomethoxylation of olefins.
Scheme 10: Benzylic azidation initiated by [Cu(I)(dap)2]Cl.
Scheme 11: Trifluoromethyl methoxylation of styryl derivatives using [Cu(I)(dap)2]PF6. All redox potentials ar...
Scheme 12: Trifluoromethylation of silyl enol ethers.
Scheme 13: Synthesis of annulated heterocycles upon oxidation with the Sauvage catalyst.
Scheme 14: Oxoazidation of styrene derivatives using [Cu(dap)2]Cl as a precatalyst.
Scheme 15: [Cu(I)(dpp)(binc)]PF6-catalyzed ATRA reaction.
Scheme 16: Allylation reaction of α-bromomalonate catalyzed by [Cu(I)(dpp)(binc)]PF6 following an ATRA mechani...
Scheme 17: Bromo/tribromomethylation reaction using [Cu(I)(dmp)(BINAP)]PF6.
Scheme 18: Chlorotrifluoromethylation of alkenes catalyzed by [Cu(I)(N^N)(xantphos)]PF6.
Scheme 19: Chlorosulfonylation of styrene and alkyne derivatives by ATRA reactions.
Scheme 20: Reduction of aryl and alkyl halides with the complex [Cu(I)(bcp)(DPEPhos)]PF6. aIrradiation was car...
Scheme 21: Meerwein arylation of electron-rich aromatic derivatives and 5-exo-trig cyclization catalyzed by th...
Scheme 22: [Cu(I)(bcp)(DPEPhos)]PF6-photocatalyzed synthesis of alkaloids. aYield over two steps (cyclization ...
Scheme 23: Copper-photocatalyzed decarboxylative amination of NHP esters.
Scheme 24: Photocatalytic decarboxylative alkynylation using [Cu(I)(dq)(binap)]BF4.
Scheme 25: Copper-photocatalyzed alkylation of glycine esters.
Scheme 26: Copper-photocatalyzed borylation of organic halides. aUnder continuous flow conditions.
Scheme 27: Copper-photocatalyzed α-functionalization of alcohols with glycine ester derivatives.
Scheme 28: δ-Functionalization of alcohols using [Cu(I)(dmp)(xantphos)]BF4.
Scheme 29: Photocatalytic synthesis of [5]helicene and phenanthrene.
Scheme 30: Oxidative carbazole synthesis using in situ-formed [Cu(I)(dmp)(xantphos)]BF4.
Scheme 31: Copper-photocatalyzed functionalization of N-aryl tetrahydroisoquinolines.
Scheme 32: Bicyclic lactone synthesis using a copper-photocatalyzed PCET reaction.
Scheme 33: Photocatalytic Pinacol coupling reaction catalyzed by [Cu(I)(pypzs)(BINAP)]BF4. The ligands of the ...
Scheme 34: Azide photosensitization using a Cu-based photocatalyst.
Beilstein J. Org. Chem. 2020, 16, 125–134, doi:10.3762/bjoc.16.14
Graphical Abstract
Figure 1: a) The potent tubulin inhibitor colchicine as a lead scaffold led to the development of the HOTub g...
Figure 2: Chemical structures of HITubs. Key variations with respect to HITub-4 are highlighted in dashed box...
Figure 3: Photocharacterisation of HITub-4. a) Photochemical and thermal isomerisation. b) UV–vis spectra aft...
Figure 4: a) Resazurin reduction assay for HITub-4 and nocodazole in HeLa cells (n = 3), demonstrating the di...
Figure 5: Confocal microscopy images of immunofluorescently labelled MT networks after treatment with HITubs ...
Figure 6: Cell cycle analysis of HITub-4-treated cells. a) and b) (Z)-HITub-4 caused significant G2/M arrest ...
Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264
Graphical Abstract
Figure 1: General classification of asymmetric electroorganic reactions.
Scheme 1: Asymmetric reduction of 4-acetylpyridine using a modified graphite cathode.
Scheme 2: Asymmetric hydrogenation of ketones using Raney nickel powder electrodes modified with optically ac...
Scheme 3: Asymmetric reduction of prochiral activated olefins with a poly-ʟ-valine-coated graphite cathode.
Scheme 4: Asymmetric reduction of prochiral carbonyl compounds, oximes and gem-dibromides on a poly-ʟ-valine-...
Scheme 5: Asymmetric hydrogenation of prochiral ketones with poly[RuIII(L)2Cl2]+-modified carbon felt cathode...
Scheme 6: Asymmetric hydrogenation of α-keto esters using chiral polypyrrole film-coated cathode incorporated...
Scheme 7: Quinidine and cinchonidine alkaloid-induced asymmetric electroreduction of acetophenone.
Scheme 8: Asymmetric electroreduction of 4- and 2-acetylpyridines at a mercury cathode in the presence of a c...
Scheme 9: Enantioselective reduction of 4-methylcoumarin in the presence of catalytic yohimbine.
Scheme 10: Cinchonine-induced asymmetric electrocarboxylation of 4-methylpropiophenone.
Scheme 11: Enantioselective hydrogenation of methyl benzoylformate using an alkaloid entrapped silver cathode.
Scheme 12: Alkaloid-induced enantioselective hydrogenation using a Cu nanoparticle cathode.
Scheme 13: Alkaloid-induced enantioselective hydrogenation of aromatic ketones using a bimetallic Pt@Cu cathod...
Scheme 14: Enantioselective reduction of ketones at mercury cathode using N,N'-dimethylquininium tetrafluorobo...
Scheme 15: Asymmetric synthesis of an amino acid using an electrode modified with amino acid oxidase and elect...
Scheme 16: Asymmetric oxidation of p-tolyl methyl sulfide using chemically modified graphite anode.
Scheme 17: Asymmetric oxidation of unsymmetric sulfides using poly(amino acid)-coated electrodes.
Scheme 18: Enantioselective, electocatalytic oxidative coupling on TEMPO-modified graphite felt electrode in t...
Scheme 19: Asymmetric electrocatalytic oxidation of racemic alcohols on a TEMPO-modified graphite felt electro...
Scheme 20: Asymmetric electrocatalytic lactonization of diols on TEMPO-modified graphite felt electrodes.
Scheme 21: Asymmetric electrochemical pinacolization in a chiral solvent.
Scheme 22: Asymmetric electroreduction using a chiral supporting electrolyte.
Scheme 23: Asymmetric anodic oxidation of enol acetates using chiral supporting electrolytes.
Scheme 24: Kinetic resolution of primary amines using a chiral N-oxyl radical mediator.
Scheme 25: Chiral N-oxyl-radical-mediated kinetic resolution of secondary alcohols via electrochemical oxidati...
Scheme 26: Chiral iodoarene-mediated asymmetric electrochemical lactonization.
Scheme 27: Os-catalyzed electrochemical asymmetric dihydroxylation of olefins using the Sharpless ligand and i...
Scheme 28: Asymmetric electrochemical epoxidation of olefins catalyzed by a chiral Mn-salen complex.
Scheme 29: Asymmetric electrooxidation of 1,2-diols, and amino alcohols using a chiral copper catalyst.
Scheme 30: Mechanism of asymmetric electrooxidation of 1,2-diols, and amino alcohols using a chiral copper cat...
Scheme 31: Enantioselective electrocarboxylation catalyzed by an electrogenerated chiral [CoI(salen)]− complex....
Scheme 32: Asymmetric oxidative cross coupling of 2-acylimidazoles with silyl enol ethers.
Scheme 33: Ni-catalyzed asymmetric electroreductive cleavage of allylic β-keto ester 89.
Scheme 34: Asymmetric alkylation using a combination of electrosynthesis and a chiral Ni catalyst.
Scheme 35: Mechanism of asymmetric alkylation using a combination of electrosynthesis and a chiral Ni catalyst....
Scheme 36: Asymmetric epoxidation by electrogenerated percarbonate and persulfate ions in the presence of chir...
Scheme 37: α-Oxyamination of aldehydes via anodic oxidation catalyzed by chiral secondary amines.
Scheme 38: The α-alkylation of aldehydes via anodic oxidation catalyzed by chiral secondary amines.
Scheme 39: Mechanism of α-alkylation of aldehydes via anodic oxidation catalyzed by chiral secondary amines.
Scheme 40: Electrochemical chiral secondary amine-catalyzed intermolecular α-arylation of aldehydes.
Scheme 41: Mechanism of electrochemical chiral secondary amine-catalyzed intermolecular α-arylation of aldehyd...
Scheme 42: Asymmetric cross-dehydrogenative coupling of tertiary amines with simple ketones via an electrochem...
Scheme 43: Electroenzymatic asymmetric reduction using enoate reductase.
Scheme 44: Assymetric reduction using alcohol dehydrogenase as the electrocatalyst.
Scheme 45: Asymmetric electroreduction catalyzed by thermophilic NAD-dependent alcohol dehydrogenase.
Scheme 46: Asymmetric epoxidation of styrene by electrochemical regeneration of flavin-dependent monooxygenase....
Scheme 47: Asymmetric electroreduction using a chloroperoxidase catalyst.
Scheme 48: Asymmetric electrochemical transformation mediated by hydrophobic vitamin B12.
Scheme 49: Diastereoselective cathodic reduction of phenylglyoxalic acids substituted with amines as chiral au...
Scheme 50: Ni-catalyzed asymmetric electroreductive cross coupling of aryl halides with α-chloropropanoic acid...
Scheme 51: Electrochemical Mannich addition of silyloxyfuran to in situ-generated N-acyliminium ions.
Scheme 52: Stereoselective electroreductive homodimerization of cinnamates attached to a camphor-derived chira...
Scheme 53: Diastereoselective electrochemical carboxylation of chiral α-bromocarboxylic acid derivatives.
Scheme 54: Electrocatalytic stereoselective conjugate addition of chiral β-dicarbonyl compounds to methyl viny...
Scheme 55: Stereoselective electrochemical carboxylation of chiral cinnamic acid derivatives under a CO2 atmos...
Scheme 56: Electrochemical diastereoselective α-alkylation of pyrrolidines attached with phosphorus-derived ch...
Scheme 57: Electrogenerated cyanomethyl anion-induced synthesis of chiral cis-β-lactams from amides bearing ch...
Scheme 58: Diastereoselective anodic oxidation followed by intramolecular cyclization of ω-hydroxyl amides bea...
Scheme 59: Electrochemical deprotonation of Ni(II) glycinate containing (S)-BPB as a chiral auxiliary: diaster...
Scheme 60: Enantioselective electroreductive coupling of diaryl ketones with α,β-unsaturated carbonyl compound...
Scheme 61: Asymmetric total synthesis of ropivacaine and its analogues using a electroorganic reaction as a ke...
Scheme 62: Asymmetric total synthesis of (−)-crispine A and its natural enantiomer via anodic cyanation of tet...
Scheme 63: Asymmetric oxidative electrodimerization of cinnamic acid derivatives as key step for the synthesis...
Beilstein J. Org. Chem. 2018, 14, 1813–1825, doi:10.3762/bjoc.14.154
Graphical Abstract
Figure 1: The structures of hypervalent iodine (III) reagents [8].
Scheme 1: Hypervalent iodine(III)-catalyzed functionalization of alkenes.
Scheme 2: Catalytic sulfonyloxylactonization of alkenoic acids [43].
Scheme 3: Catalytic diacetoxylation of alkenes [46].
Scheme 4: Intramolecular asymmetric dioxygenation of alkenes [48,50].
Scheme 5: Intermolecular asymmetric diacetoxylation of styrenes [52].
Scheme 6: Diacetoxylation of alkenes with ester groups containing catalysts 17 [55].
Scheme 7: Intramolecular diamination of alkenes [56].
Scheme 8: Intramolecular asymmetric diamination of alkenes [57].
Scheme 9: Intermolecular asymmetric diamination of alkenes [58].
Scheme 10: Iodoarene-catalyzed aminofluorination of alkenes [60,61].
Scheme 11: Iodoarene-catalyzed aminofluorination of alkenes [62].
Scheme 12: Catalytic difluorination of alkenes with Selectfluor [63].
Scheme 13: Iodoarene-catalyzed 1,2-difluorination of alkenes [64].
Scheme 14: Iodoarene-catalyzed asymmetric fluorination of styrenes [64,65].
Scheme 15: Gem-difluorination of styrenes [67].
Scheme 16: Asymmetric gem-difluorination of cinnamic acid derivatives [68].
Scheme 17: Oxyarylation of alkenes [71].
Scheme 18: Asymmetric oxidative rearrangements of alkenes [72].
Scheme 19: Bromolactonization of alkenes [75].
Scheme 20: Bromination of alkenes [77,78].
Scheme 21: Cooperative strategy for the carbonylation of alkenes [79].
Beilstein J. Org. Chem. 2018, 14, 861–868, doi:10.3762/bjoc.14.72
Graphical Abstract
Scheme 1: Anodic oxidation of amides.
Scheme 2: Anodic oxidation of an amide in the presence of alkene.
Scheme 3: Intramolecular cyclization via anodic oxidation of an eneamide.
Scheme 4: Anodic bond cleavages in amides of type Ph2CHCONHAr.
Scheme 5: Type of products obtained (n = 0, 1, 2).
Scheme 6: Synthesized cyclic N-acyl and N-sulfonyl piperidines for electrolysis.
Scheme 7: Type of bisamides (derived from diamines) studied (n = 2, 3, 4).
Scheme 8: Type of products obtained from anodic oxidation of II-3.
Scheme 9: Anodic splitting of C–C bond in bisamides in the presence of LiClO4 electrolyte.
Scheme 10: Anodic splitting of C–C bond in bisamides in the presence of Et4NBF4 electrolyte.
Scheme 11: A suggested mechanism for anodic methoxylation of amides.
Scheme 12: Mechanisms of formation of fragmentation products.
Beilstein J. Org. Chem. 2018, 14, 389–396, doi:10.3762/bjoc.14.27
Graphical Abstract
Figure 1: Cyclic voltammograms of 0.1 M Bu4NBF4/MeCN with a Pt disk working electrode in the absence (brown l...
Figure 2: Calculated HOMO diagram of 1a.
Figure 3: Calculated HOMO diagrams of 1h, 1i and 1j.
Scheme 1: Plausible reaction paths of the anodic oxidation of 1i in Et4NF·4HF/CH2Cl2.
Scheme 2: Anodic fluorination of 1k.
Scheme 3: Anodic fluorination of cyclic derivative 1l.
Scheme 4: Anodic oxidation of 1m and 1n in Et4NF·4HF/CH2Cl2.
Scheme 5: General reaction mechanism for the anodic fluorination of 1.
Scheme 6: Reaction mechanism for the anodic oxidation of carboxylic acids 1m and 1n in the presence of a fluo...
Beilstein J. Org. Chem. 2017, 13, 2659–2662, doi:10.3762/bjoc.13.263
Graphical Abstract
Scheme 1: Diels–Alder reaction of isobenzofuran and formation of a benzene ring in the cycloadduct.
Scheme 2: Different approaches for the synthesis of IBF (1).
Scheme 3: Reaction of in situ prepared IBF (1) with DMAD (9).
Beilstein J. Org. Chem. 2017, 13, 1446–1455, doi:10.3762/bjoc.13.142
Graphical Abstract
Scheme 1: α-Amidoalkylation reactions under basic or acidic conditions.
Scheme 2: Synthetic routes of α-amido- and α-imidoalkylation of aromatic and heteroaromatic compounds.
Scheme 3: Reaction of imidophosphonium salt 5e with 1,3,5-trimethoxybenzene.
Beilstein J. Org. Chem. 2016, 12, 1170–1177, doi:10.3762/bjoc.12.112
Graphical Abstract
Scheme 1: Synthesis of highly functionalized 2,2'-bipyridines 4a and 5b from symmetrical 1,3-diketones 1a and ...
Scheme 2: Synthesis of β-ketoenamines 2c–e and of β-ketoenamides 3c–h.
Scheme 3: Synthesis of α-methoxy-β-ketoenamine 2i, its N-acylation to 3i and the reaction of β-ketoenamide 3a...
Scheme 4: Cyclizations of β-ketoenamide 3i leading to 2,2´-bipyridine derivative 4i or to the related 2-(2-py...
Scheme 5: Suzuki-couplings of 2,2'-bipyrid-4-yl nonaflates 5a and 5b to compounds 9 and 10.
Scheme 6: Palladium-catalyzed couplings of chloro-substituted 2,2'-bipyrid-4-yl nonaflate 5g leading to compo...
Beilstein J. Org. Chem. 2015, 11, 2132–2144, doi:10.3762/bjoc.11.230
Graphical Abstract
Scheme 1: Copper-catalyzed C–H bond halogenation of 2-arylpyridine.
Scheme 2: ortho-Chlorination of 2-arylpridines with acyl chlorides.
Scheme 3: Copper-catalyzed chlorination of 2-arylpyridines using LiCl.
Scheme 4: Copper-catalyzed C–H halogenation of 2-arylpyridines using LiX.
Scheme 5: Copper-mediated selective C–H halogenations of 2-arylpyridine.
Scheme 6: Copper-catalyzed C–H o-halogenation using removable DG.
Scheme 7: Copper-catalyzed C–H halogenations using PIP as DG.
Scheme 8: Copper-catalyzed quinoline C–H chlorination.
Scheme 9: Copper-catalyzed arene C–H fluorination of benzamides.
Scheme 10: Copper-catalyzed arene C–H iodination of 1,3-azoles.
Scheme 11: Copper-catalyzed C–H halogenations of phenols.
Scheme 12: Proposed mechanism for the C–H halogenation of phenols.
Scheme 13: Copper-catalyzed halogenation of electron enriched arenes.
Scheme 14: Copper-catalyzed C–H bromination of arenes.
Scheme 15: CuI-mediated synthesis of iododibenzo[b,d]furans via C–H functionalization.
Scheme 16: Cu-Mn spinel oxide-catalyzed phenol and heteroarene halogenation.
Scheme 17: Copper-catalyzed halogenations of 2-amino-1,3thiazoles.
Scheme 18: Copper-mediated chlorination and bromination of indolizines.
Scheme 19: Copper-catalyzed three-component synthesis of bromoindolizines.
Scheme 20: Copper-mediated C–H halogenation of azacalix[1]arene[3]pyridines.
Scheme 21: Copper-mediated cascade synthesis of halogenated pyrrolones.
Scheme 22: Copper-mediated alkene C–H chlorination in spirothienooxindole.
Scheme 23: Copper-catalyzed remote C–H chlorination of alkyl hydroperoxides.
Scheme 24: Copper-catalyzed C–H fluorination of alkanes.
Scheme 25: Copper-catalyzed or mediated C–H halogenations of active C(sp3)-bonds.
Beilstein J. Org. Chem. 2015, 11, 1418–1424, doi:10.3762/bjoc.11.153
Graphical Abstract
Figure 1: General structure of bisphosphonates.
Figure 2: General structures of 1-hydroxy- and 1-amino-1-phosphinylalkylphosphonates (2 and 3, respectively) ...
Scheme 1: Electrochemical α-methoxylation of 1-(N-acylamino)alkylphosphonates.
Scheme 2: Transformation of diethyl 1-(N-acetylamino)-1-methoxyalkylphosphonates into bisphosphoric acid este...
Beilstein J. Org. Chem. 2015, 11, 1241–1245, doi:10.3762/bjoc.11.138
Graphical Abstract
Scheme 1: A strategy for developing functionalized nitrile oxides.
Figure 1: Versatile functionalized nitrile oxides.
Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13
Graphical Abstract
Scheme 1: Cross-dehydrogenative coupling.
Scheme 2: Cross-dehydrogenative C–O coupling.
Scheme 3: Regioselective ortho-acetoxylation of meta-substituted arylpyridines and N-arylamides.
Scheme 4: ortho-Acyloxylation and alkoxylation of arenes directed by pyrimidine, benzoxazole, benzimidazole a...
Scheme 5: Cu(OAc)2/AgOTf/O2 oxidative system in the ortho-alkoxylation of arenes.
Scheme 6: Pd(OAc)2/persulfate oxidative system in the ortho-alkoxylation and acetoxylation of arenes with nit...
Scheme 7: ortho-Acetoxylation and methoxylation of O-methyl aryl oximes, N-phenylpyrrolidin-2-one, and (3-ben...
Scheme 8: Ruthenium-catalyzed ortho-acyloxylation of acetanilides.
Scheme 9: Acetoxylation and alkoxylation of arenes with amide directing group using Pd(OAc)2/PhI(OAc)2 oxidat...
Scheme 10: Alkoxylation of azoarenes, 2-aryloxypyridines, picolinamides, and N-(1-methyl-1-(pyridin-2-yl)ethyl...
Scheme 11: Acetoxylation of compounds containing picolinamide and quinoline-8-amine moieties using the Pd(OAc)2...
Scheme 12: (CuOH)2CO3 catalyzed oxidative ortho-etherification using air as oxidant.
Scheme 13: Copper-catalyzed aerobic alkoxylation and aryloxylation of arenes containing pyridine-N-oxide moiet...
Scheme 14: Cobalt-catalyzed aerobic alkoxylation of arenes and alkenes containing pyridine N-oxide moiety.
Scheme 15: Non-symmetric double-fold C–H ortho-acyloxylation.
Scheme 16: N-nitroso directed ortho-alkoxylation of arenes.
Scheme 17: Selective alkoxylation and acetoxylation of alkyl groups.
Scheme 18: Acetoxylation of 2-alkylpyridines and related compounds.
Scheme 19: Acyloxylation and alkoxylation of alkyl fragments of substrates containing amide or sulfoximine dir...
Scheme 20: Palladium-catalyzed double sp3 C–H alkoxylation of N-(quinolin-8-yl)amides for the synthesis of sym...
Scheme 21: Copper-catalyzed acyloxylation of methyl groups of N-(quinolin-8-yl)amides.
Scheme 22: One-pot acylation and sp3 C–H acetoxylation of oximes.
Scheme 23: Possible mechanism of oxidative esterification catalyzed by N-heterocyclic nucleophilic carbene.
Scheme 24: Oxidative esterification employing stoichiometric amounts of aldehydes and alcohols.
Scheme 25: Selective oxidative coupling of aldehydes with alcohols in the presence of amines.
Scheme 26: Iodine mediated oxidative esterification.
Scheme 27: Oxidative C–O coupling of benzyl alcohols with methylarenes under the action of Bu4NI/t-BuOOH syste...
Scheme 28: Oxidative coupling of methyl- and ethylarenes with aromatic aldehydes under the action of Bu4NI/t-B...
Scheme 29: Cross-dehydrogenative C–O coupling of aldehydes with t-BuOOH in the presence of Bu4NI.
Scheme 30: Bu4NI-catalyzed α-acyloxylation reaction of ethers and ketones with aldehydes and t-BuOOH.
Scheme 31: Oxidative coupling of aldehydes with N-hydroxyimides and hexafluoroisopropanol.
Scheme 32: Oxidative coupling of alcohols with N-hydroxyimides.
Scheme 33: Oxidative coupling of aldehydes and primary alcohols with N-hydroxyimides using (diacetoxyiodo)benz...
Scheme 34: Proposed mechanism of the oxidative coupling of aldehydes and N-hydroxysuccinimide under action of ...
Scheme 35: Oxidative coupling of aldehydes with pivalic acid (172).
Scheme 36: Oxidative C–O coupling of aldehydes with alkylarenes using the Cu(OAc)2/t-BuOOH system.
Scheme 37: Copper-catalyzed acyloxylation of C(sp3)-H bond adjacent to oxygen in ethers using benzyl alcohols.
Scheme 38: Oxidative C–O coupling of aromatic aldehydes with cycloalkanes.
Scheme 39: Ruthenium catalyzed cross-dehydrogenative coupling of primary and secondary alcohols.
Scheme 40: Cross-dehydrogenative C–O coupling reactions of β-dicarbonyl compounds with sulfonic acids, acetic ...
Scheme 41: Acyloxylation of ketones, aldehydes and β-dicarbonyl compounds using carboxylic acids and Bu4NI/t-B...
Scheme 42: Acyloxylation of ketones using Bu4NI/t-BuOOH system.
Scheme 43: Cross-dehydrogenative C–O coupling of β-dicarbonyl compounds and their heteroanalogues with N-hydro...
Scheme 44: Cross-dehydrogenative C–O coupling of β-dicarbonyl compounds and their heteroanalogues with t-BuOOH....
Scheme 45: Oxidative C–O coupling of 2,6-dialkylphenyl-β-keto esters and thioesters with tert-butyl hydroxycar...
Scheme 46: α’-Acyloxylation of α,β-unsaturated ketones using KMnO4.
Scheme 47: Possible mechanisms of the acetoxylation at the allylic position of alkenes by Pd(OAc)2.
Scheme 48: Products of the oxidation of terminal alkenes by Pd(II)/AcOH/oxidant system.
Scheme 49: Acyloxylation of terminal alkenes with carboxylic acids.
Scheme 50: Synthesis of linear E-allyl esters by cross-dehydrogenative coupling of terminal alkenes wih carbox...
Scheme 51: Pd(OAc)2-catalyzed acetoxylation of Z-vinyl(triethylsilanes).
Scheme 52: α’-Acetoxylation of α-acetoxyalkenes with copper(II) chloride in acetic acid.
Scheme 53: Oxidative acyloxylation at the allylic position of alkenes and at the benzylic position of alkylare...
Scheme 54: Copper-catalyzed alkoxylation of methylheterocyclic compounds using di-tert-butylperoxide as oxidan...
Scheme 55: Oxidative C–O coupling of methylarenes with β-dicarbonyl compounds or phenols.
Scheme 56: Copper-catalyzed esterification of methylbenzenes with cyclic ethers and cycloalkanes.
Scheme 57: Oxidative C–O coupling of carboxylic acids with toluene catalyzed by Pd(OAc)2.
Scheme 58: Oxidative acyloxylation at the allylic position of alkenes with carboxylic acids using the Bu4NI/t-...
Scheme 59: Cross-dehydrogenative C–O coupling of carboxylic acids with alkylarenes using the Bu4NI/t-BuOOH sys...
Scheme 60: Oxidative C–O cross-coupling of methylarenes with ethyl or isopropylarenes.
Scheme 61: Phosphorylation of benzyl C–H bonds using the Bu4NI/t-BuOOH oxidative system.
Scheme 62: Selective C–H acetoxylation of 2,3-disubstituted indoles.
Scheme 63: Acetoxylation of benzylic position of alkylarenes using DDQ as oxidant.
Scheme 64: C–H acyloxylation of diarylmethanes, 3-phenyl-2-propen-1-yl acetate and dimethoxyarene using DDQ.
Scheme 65: Cross-dehydrogenative C–O coupling of 1,3-diarylpropylenes and 1,3-diarylpropynes with alcohols.
Scheme 66: One-pot azidation and C–H acyloxylation of 3-chloro-1-arylpropynes.
Scheme 67: Cross-dehydrogenative C–O coupling of 1,3-diarylpropylenes, (E)-1-phenyl-2-isopropylethylene and is...
Scheme 68: Cross-dehydrogenative C–O coupling of alkylarenes and related compounds with N-hydroxyphthalimide.
Scheme 69: Acetoxylation at the benzylic position of alkylarenes mediated by N-hydroxyphthalimide.
Scheme 70: C–O coupling of methylarenes with aromatic carboxylic acids employing the NaBrO3/NaHSO3 system.
Scheme 71: tert-Butyl peroxidation of allyl, propargyl and benzyl ethers catalyzed by Fe(acac)3.
Scheme 72: Cross-dehydrogenative C–O coupling of ethers with carboxylic acids mediated by Bu4NI/t-BuOOH system....
Scheme 73: Oxidative acyloxylation of dimethylamides and dioxane with 2-aryl-2-oxoacetic acids accompanied by ...
Scheme 74: tert-Butyl peroxidation of N-benzylamides and N-allylbenzamide using the Bu4NI/t-BuOOH system.
Scheme 75: Cross-dehydrogenative C–O coupling of aromatic carboxylic acids with ethers using Fe(acac)3 as cata...
Scheme 76: Cross-dehydrogenative C–O coupling of cyclic ethers with 2-hydroxybenzaldehydes using iron carbonyl...
Scheme 77: Cross-dehydrogenative C–O coupling of ethers with β-dicarbonyl compounds and phenols using copper c...
Scheme 78: Cross-dehydrogenative C–O coupling of 2-hydroxybenzaldehyde with dioxane catalyzed by Cu2(BPDC)2(BP...
Scheme 79: Ruthenium chloride-catalyzed acyloxylation of β-lactams.
Scheme 80: Ruthenium-catalyzed tert-butyl peroxydation amides and acetoxylation of β-lactams.
Scheme 81: PhI(OAc)2-mediated α,β-diacetoxylation of tertiary amines.
Scheme 82: Electrochemical oxidative methoxylation of tertiary amines.
Scheme 83: Cross-dehydrogenative C–O coupling of ketene dithioacetals with carboxylic acids in the presence of...
Scheme 84: Cross-dehydrogenative C–O coupling of enamides with carboxylic acids using iodosobenzene as oxidant....
Scheme 85: Oxidative alkoxylation, acetoxylation, and tosyloxylation of acylanilides using PhI(O(O)CCF3)2 in t...
Scheme 86: Proposed mechanism of the oxidative C–O coupling of actetanilide with O-nucleophiles in the presenc...
Scheme 87: Three-component coupling of aldehydes, anilines and alcohols involving oxidative intermolecular C–O...
Scheme 88: Oxidative coupling of phenols with alcohols.
Scheme 89: 2-Acyloxylation of quinoline N-oxides with arylaldehydes in the presence of the CuOTf/t-BuOOH syste...
Scheme 90: Cross-dehydrogenative C–O coupling of azoles with primary alcohols.
Scheme 91: Oxidation of dipyrroles to dipyrrins and subsequent oxidative alkoxylation in the presence of Na3Co...
Scheme 92: Oxidative dehydrogenative carboxylation of alkanes and cycloalkanes to allylic esters.
Scheme 93: Pd-catalyzed acetoxylation of benzene.
Beilstein J. Org. Chem. 2014, 10, 3056–3072, doi:10.3762/bjoc.10.323
Graphical Abstract
Scheme 1: Application of anodic oxidation to the generation of new carbon-carbon bonds [11].
Scheme 2: The influence of the amino protecting group on the “kinetic” and “thermodynamic” anodic methoxylati...
Scheme 3: Example of the application of the cation pool method [17].
Scheme 4: A thiophenyl electroauxiliary allows for regioselective anodic oxidation [32].
Scheme 5: A diastereoselective cation carbohydroxylation reaction and postulated intermediate 18 [18].
Scheme 6: A radical addition and electron transfer reaction of N-acyliminium ions generated electrosynthetica...
Scheme 7: Catalytic indirect anodic fluorodesulfurization reaction [37].
Figure 1: Schematic of a cation flow system and also shown is the electrochemical microflow reactor reported ...
Figure 2: Example of a parallel laminar flow set-up. Figure redrawn from reference [38].
Figure 3: A catch and release cation pool method [42].
Scheme 8: Micromixing effects on yield 92% vs 36% and ratio of alkylation products [43].
Figure 4: Schematic illustration of the anodic substitution reaction system using acoustic emulsification. Fi...
Scheme 9: Electrooxidation to prepare a chiral oxidation mediator and application to the kinetic resolution o...
Scheme 10: Electrooxidation reactions on 4-membered ring systems [68].
Figure 5: Example of a chiral auxiliary Shono-oxidation intermediate [69].
Scheme 11: An electrochemical multicomponent reaction where a carbon felt anode and platinum cathode were util...
Scheme 12: Preparation of dienes using the Shono oxidation [23].
Scheme 13: Combination of an electroauxiliary mediated anodic oxidation and RCM to afford spirocyclic compound...
Scheme 14: Total synthesis of (+)-myrtine (66) using an electrochemical approach [78].
Scheme 15: Total synthesis of (−)-A58365A (70) and (±)-A58365B (71) [79].
Scheme 16: Anodic oxidation used in the preparation of the poison frog alkaloid 195C [80].
Scheme 17: Preparation of iminosugars using an electrochemical approach [81].
Scheme 18: The electrosynthetic preparation of α-L-fucosidase inhibitors [84,85].
Scheme 19: Enantioselective synthesis of the anaesthetic ropivacaine 85 [71].
Scheme 20: The preparation of synthetically challenging aza-nucleosides employing an electrochemical step [88].
Scheme 21: Synthesis of a bridged tricyclic diproline analogue 93 that induces α-helix conformation into linea...
Scheme 22: Synthesis of (i) a peptidomimetic and (ii) a functionalised peptide from silyl electroauxiliary pre...
Scheme 23: Examples of Phe7–Phe8 mimics prepared using an electrochemical approach [93].
Scheme 24: Preparation of arginine mimics employing an electrooxidation step [96].
Scheme 25: Preparation of chiral cyclic amino acids [20].
Scheme 26: Two-step preparation of Nazlinine 117 using Shono flow electrochemistry [101].
Beilstein J. Org. Chem. 2013, 9, 791–799, doi:10.3762/bjoc.9.90
Graphical Abstract
Figure 1: The structures investigated in the amination of heterocyclic and carbocyclic derivatives (series A ...
Figure 2: –log k as a function of SS in water for series A and B.
Figure 3: The structures investigated in the methoxylation of polychlorofluorobenzene derivatives (series C) ...
Figure 4: −log k as a function of SS in methanol for series C.
Figure 5: Optimized geometries, relative energies, and imaginary frequencies for the transition states and th...
Beilstein J. Org. Chem. 2011, 7, 1108–1114, doi:10.3762/bjoc.7.127
Graphical Abstract
Scheme 1: Electrochemically generated N-acyliminium ions 1 and subsequent reactions.
Figure 1: Electrochemical microreactor.
Scheme 2: Electrolysis of furan.
Scheme 3: Kolbe electrolysis of phenylacetic acids 6 in flow.
Scheme 4: Synthesis of diaryliodonium salts 11 in flow.
Beilstein J. Org. Chem. 2008, 4, No. 34, doi:10.3762/bjoc.4.34
Graphical Abstract
Figure 1: A collection of the structural diversity seen in the vibsanin type diterpene family.
Figure 2: Vibsanin type diterpene synthetic targets.
Scheme 1: Retrosynthesis of vibsanin type targets.
Scheme 2: The four functional group areas identified for investigation.
Scheme 3: Acetone sidechain studies.
Figure 3: ORTEP diagrams of compounds 24 and 23 (30% probability elipsoids).
Scheme 4: α-Hydroxylation investigations.
Figure 4: ORTEP diagram of compound 32 (30% probability ellipsoids).
Scheme 5: Investigating literature methods to install the furan ring system.
Scheme 6: Installation of the furan ring system continued.
Scheme 7: Installation of the enol sidechain utilizing Wittig chemistry.
Scheme 8: Attempts to gain access to targets 50 and 51.
Scheme 9: Further attempts to gain access to target compound 51.