Search for "platinum" in Full Text gives 193 result(s) in Beilstein Journal of Organic Chemistry.
Beilstein J. Org. Chem. 2025, 21, 1272–1305, doi:10.3762/bjoc.21.99
Graphical Abstract
Figure 1: a) Stone–Wales (red) and azulene (blue) defects in graphene; b) azulene and its selected resonance ...
Figure 2: Examples of azulene-embedded 2D allotropic forms of carbon: a) phagraphene and b) TPH-graphene.
Scheme 1: Synthesis of non-alternant isomers of pyrene (2 and 6) using dehydrogenation.
Scheme 2: Synthesis of non-alternant isomer 9 of benzo[a]pyrene and 14 of benzo[a]perylene using dehydrogenat...
Scheme 3: Synthesis of azulene-embedded isomers of benzo[a]pyrene (18 and 22) inspired by Ziegler–Hafner azul...
Figure 3: General strategies leading to azulene-embedded nanographenes: a) construction of azulene moiety in ...
Scheme 4: Synthesis of biradical PAHs possessing significant biradical character using oxidation of partially...
Scheme 5: Synthesis of dicyclohepta[ijkl,uvwx]rubicene (29) and its further modifications.
Scheme 6: Synthesis of warped PAHs with one embedded azulene subunit using Scholl-type oxidation.
Scheme 7: Synthesis of warped PAHs with two embedded azulene subunits using Scholl oxidation.
Scheme 8: Synthesis of azulene-embedded PAHs using [3 + 2] annulation accompanied by ring expansion.
Scheme 9: Synthesis of azulene-embedded isomers of linear acenes using [3 + 2] annulation accompanied by ring...
Scheme 10: Synthesis of azulene-embedded PAHs using intramolecular C–H arylation.
Scheme 11: Synthesis of azulene-embedded isomers of acenes using intramolecular C–H arylation.
Scheme 12: Synthesis of azulene-embedded PAHs using intramolecular condensations.
Scheme 13: Synthesis of azulene-embedded PAH 89 using palladium-catalysed [5 + 2] annulation.
Scheme 14: Synthesis of azulene-embedded PAHs using oxidation of substituents around the azulene core.
Scheme 15: Synthesis of azulene-embedded PAHs using the oxidation of reactive positions 1 and 3 of azulene sub...
Scheme 16: Synthesis of azulene-embedded PAHs using intramolecular C–H arylation.
Scheme 17: Synthesis of an azulene-embedded isomer of terylenebisimide using tandem Suzuki coupling and C–H ar...
Scheme 18: Synthesis of azulene embedded PAHs using a bismuth-catalyzed cyclization of alkenes.
Scheme 19: Synthesis of azulene-embedded nanographenes using intramolecular cyclization of alkynes.
Scheme 20: Synthesis of azulene-embedded graphene nanoribbons and azulene-embedded helicenes using annulation ...
Scheme 21: Synthesis of azulene-fused acenes.
Scheme 22: Synthesis of non-alternant isomer of perylene 172 using Yamamoto-type homocoupling.
Scheme 23: Synthesis of N- and BN-nanographenes with embedded azulene unit(s).
Scheme 24: On-surface synthesis of azulene-embedded nanographenes from benzenoid precursors via dehydrogenatio...
Scheme 25: On-surface synthesis of azulene-embedded nanographenes from benzenoid precursors.
Scheme 26: On-surface synthesis of azulene-embedded nanoribbons.
Beilstein J. Org. Chem. 2025, 21, 1207–1271, doi:10.3762/bjoc.21.98
Graphical Abstract
Scheme 1: DTBP-mediated oxidative alkylarylation of activated alkenes.
Scheme 2: Iron-catalyzed oxidative 1,2-alkylarylation.
Scheme 3: Possible mechanism for the iron-catalyzed oxidative 1,2-alkylation of activated alkenes.
Scheme 4: A metal-free strategy for synthesizing 3,3-disubstituted oxindoles.
Scheme 5: Iminoxyl radical-promoted cascade oxyalkylation/alkylarylation of alkenes.
Scheme 6: Proposed mechanism for the iminoxyl radical-promoted cascade oxyalkylation/alkylarylation of alkene...
Scheme 7: Bicyclization of 1,n-enynes with alkyl nitriles.
Scheme 8: Possible reaction mechanism for the bicyclization of 1,n-enynes with alkyl nitriles.
Scheme 9: Radical cyclization of N-arylacrylamides with isocyanides.
Scheme 10: Plausible mechanism for the radical cyclization of N-arylacrylamides with isocyanides.
Scheme 11: Electrochemical dehydrogenative cyclization of 1,3-dicarbonyl compounds.
Scheme 12: Plausible mechanism for the dehydrogenative cyclization of 1,3-dicarbonyl compounds.
Scheme 13: Photocatalyzed cyclization of N-arylacrylamide and N,N-dimethylaniline.
Scheme 14: Proposed mechanism for the photocatalyzed cyclization of N-arylacrylamides and N,N-dimethylanilines....
Scheme 15: Electrochemical monofluoroalkylation cyclization of N-arylacrylamides with dimethyl 2-fluoromalonat...
Scheme 16: Proposed mechanism for the electrochemical radical cyclization of N-arylacrylamides with dimethyl 2...
Scheme 17: Photoelectrocatalytic carbocyclization of unactivated alkenes using simple malonates.
Scheme 18: Plausible mechanism for the photoelectrocatalytic carbocyclization of unactivated alkenes with simp...
Scheme 19: Bromide-catalyzed electrochemical trifluoromethylation/cyclization of N-arylacrylamides.
Scheme 20: Proposed mechanism for the electrochemical trifluoromethylation/cyclization of N-arylacrylamides.
Scheme 21: Visible light-mediated trifluoromethylarylation of N-arylacrylamides.
Scheme 22: Plausible reaction mechanism for the visible light-mediated trifluoromethylarylation of N-arylacryl...
Scheme 23: Electrochemical difluoroethylation cyclization of N-arylacrylamides with sodium difluoroethylsulfin...
Scheme 24: Electrochemical difluoroethylation cyclization of N-methyacryloyl-N-alkylbenzamides with sodium dif...
Scheme 25: Photoredox-catalyzed radical aryldifluoromethylation of N-arylacrylamides with S-(difluoromethyl)su...
Scheme 26: Proposed mechanism for the photoredox-catalyzed radical aryldifluoromethylation of N-arylacrylamide...
Scheme 27: Visible-light-induced domino difluoroalkylation/cyclization of N-cyanamide alkenes.
Scheme 28: Proposed mechanism of photoredox-catalyzed radical domino difluoroalkylation/cyclization of N-cyana...
Scheme 29: Palladium-catalyzed oxidative difunctionalization of alkenes.
Scheme 30: Two possible mechanisms of palladium-catalyzed oxidative difunctionalization.
Scheme 31: Silver-catalyzed oxidative 1,2-alkyletherification of unactivated alkenes with α-bromoalkylcarbonyl...
Scheme 32: Photochemical radical cascade cyclization of dienes.
Scheme 33: Proposed mechanism for the photochemical radical cascade 6-endo cyclization of dienes with α-carbon...
Scheme 34: Photocatalyzed radical coupling/cyclization of N-arylacrylamides and.
Scheme 35: Photocatalyzed radical-type couplings/cyclization of N-arylacrylamides with sulfoxonium ylides.
Scheme 36: Possible mechanism of visible-light-induced radical-type couplings/cyclization of N-arylacrylamides...
Scheme 37: Visible-light-promoted difluoroalkylated oxindoles systhesis via EDA complexes.
Scheme 38: Possible mechanism for the visible-light-promoted radical cyclization of N-arylacrylamides with bro...
Scheme 39: A dicumyl peroxide-initiated radical cascade reaction of N-arylacrylamide with DCM.
Scheme 40: Possible mechanism of radical cyclization of N-arylacrylamides with DCM.
Scheme 41: An AIBN-mediated radical cascade reaction of N-arylacrylamides with perfluoroalkyl iodides.
Scheme 42: Possible mechanism for the reaction with perfluoroalkyl iodides.
Scheme 43: Photoinduced palladium-catalyzed radical annulation of N-arylacrylamides with alkyl halides.
Scheme 44: Radical alkylation/cyclization of N-Alkyl-N-methacryloylbenzamides with alkyl halides.
Scheme 45: Possible mechanism for the alkylation/cyclization with unactivated alkyl chlorides.
Scheme 46: Visible-light-driven palladium-catalyzed radical cascade cyclization of N-arylacrylamides with unac...
Scheme 47: NHC-catalyzed radical cascade cyclization of N-arylacrylamides with alkyl bromides.
Scheme 48: Possible mechanism of NHC-catalyzed radical cascade cyclization.
Scheme 49: Electrochemically mediated radical cyclization reaction of N-arylacrylamides with freon-type methan...
Scheme 50: Proposed mechanistic pathway of electrochemically induced radical cyclization reaction.
Scheme 51: Redox-neutral photoinduced radical cascade cylization of N-arylacrylamides with unactivated alkyl c...
Scheme 52: Proposed mechanistic hypothesis of redox-neutral radical cascade cyclization.
Scheme 53: Thiol-mediated photochemical radical cascade cylization of N-arylacrylamides with aryl halides.
Scheme 54: Proposed possible mechanism of thiol-mediated photochemical radical cascade cyclization.
Scheme 55: Visible-light-induced radical cascade bromocyclization of N-arylacrylamides with NBS.
Scheme 56: Possible mechanism of visible-light-induced radical cascade cyclization.
Scheme 57: Decarboxylation/radical C–H functionalization by visible-light photoredox catalysis.
Scheme 58: Plausible mechanism of visible-light photoredox-catalyzed radical cascade cyclization.
Scheme 59: Visible-light-promoted tandem radical cyclization of N-arylacrylamides with N-(acyloxy)phthalimides....
Scheme 60: Plausible mechanism for the tandem radical cyclization reaction.
Scheme 61: Visible-light-induced aerobic radical cascade alkylation/cyclization of N-arylacrylamides with alde...
Scheme 62: Plausible mechanism for the aerobic radical alkylarylation of electron-deficient amides.
Scheme 63: Oxidative decarbonylative [3 + 2]/[5 + 2] annulation of N-arylacrylamide with vinyl acids.
Scheme 64: Plausible mechanism for the decarboxylative (3 + 2)/(5 + 2) annulation between N-arylacrylamides an...
Scheme 65: Rhenium-catalyzed alkylarylation of alkenes with PhI(O2CR)2.
Scheme 66: Plausible mechanism for the rhenium-catalyzed decarboxylative annulation of N-arylacrylamides with ...
Scheme 67: Visible-light-induced one-pot tandem reaction of N-arylacrylamides.
Scheme 68: Plausible mechanism for the visible-light-initiated tandem synthesis of difluoromethylated oxindole...
Scheme 69: Copper-catalyzed redox-neutral cyanoalkylarylation of activated alkenes with cyclobutanone oxime es...
Scheme 70: Plausible mechanism for the copper-catalyzed cyanoalkylarylation of activated alkenes.
Scheme 71: Photoinduced alkyl/aryl radical cascade for the synthesis of quaternary CF3-attached oxindoles.
Scheme 72: Plausible photoinduced electron-transfer (PET) mechanism.
Scheme 73: Photoinduced cerium-mediated decarboxylative alkylation cascade cyclization.
Scheme 74: Plausible reaction mechanism for the decarboxylative radical-cascade alkylation/cyclization.
Scheme 75: Metal-free oxidative tandem coupling of activated alkenes.
Scheme 76: Control experiments and possible mechanism for 1,2-carbonylarylation of alkenes with carbonyl C(sp2...
Scheme 77: Silver-catalyzed acyl-arylation of activated alkenes with α-oxocarboxylic acids.
Scheme 78: Proposed mechanism for the decarboxylative acylarylation of acrylamides.
Scheme 79: Visible-light-mediated tandem acylarylation of olefines with carboxylic acids.
Scheme 80: Proposed mechanism for the radical cascade cyclization with acyl radical via visible-light photored...
Scheme 81: Erythrosine B-catalyzed visible-light photoredox arylation-cyclization of N-arylacrylamides with ar...
Scheme 82: Electrochemical cobalt-catalyzed radical cyclization of N-arylacrylamides with arylhydrazines or po...
Scheme 83: Proposed mechanism of radical cascade cyclization via electrochemical cobalt catalysis.
Scheme 84: Copper-catalyzed oxidative tandem carbamoylation/cyclization of N-arylacrylamides with hydrazinecar...
Scheme 85: Proposed reaction mechanism for the radical cascade cyclization by copper catalysis.
Scheme 86: Visible-light-driven radical cascade cyclization reaction of N-arylacrylamides with α-keto acids.
Scheme 87: Proposed mechanism of visible-light-driven cascade cyclization reaction.
Scheme 88: Peroxide-induced radical carbonylation of N-(2-methylallyl)benzamides with methyl formate.
Scheme 89: Proposed cyclization mechanism of peroxide-induced radical carbonylation with N-(2-methylallyl)benz...
Scheme 90: Persulfate promoted carbamoylation of N-arylacrylamides and N-arylcinnamamides.
Scheme 91: Proposed mechanism for the persulfate promoted radical cascade cyclization reaction of N-arylacryla...
Scheme 92: Photocatalyzed carboacylation with N-arylpropiolamides/N-alkyl acrylamides.
Scheme 93: Plausible mechanism for the photoinduced carboacylation of N-arylpropiolamides/N-alkyl acrylamides.
Scheme 94: Electrochemical Fe-catalyzed radical cyclization with N-arylacrylamides.
Scheme 95: Plausible mechanism for the electrochemical Fe-catalysed radical cyclization of N-phenylacrylamide.
Scheme 96: Substrate scope of the selective functionalization of various α-ketoalkylsilyl peroxides with metha...
Scheme 97: Proposed reaction mechanism for the Fe-catalyzed reaction of alkylsilyl peroxides with methacrylami...
Scheme 98: EDA-complex mediated C(sp2)–C(sp3) cross-coupling of TTs and N-methyl-N-phenylmethacrylamides.
Scheme 99: Proposed mechanism for the synthesis of oxindoles via EDA complex.
Beilstein J. Org. Chem. 2025, 21, 1116–1125, doi:10.3762/bjoc.21.89
Graphical Abstract
Figure 1: Schematic depiction of the α-CD channels containing the polyionic {[K(OH2)6]+[AuBr4]−}n chain insid...
Figure 2: Complexes of α-CD with MAuBr4 salts. Left) Co-precipitation yields from aqueous solutions of α-CD (...
Figure 3: Crystal structures of the complexes of α-CD with KAuCN2 salts, with tubular representation for α-CD...
Figure 4: Solid-state structure of the complex 2β-CD·HAuBr4·DBC. (a) Capped-stick and space-filling represent...
Figure 5: Schematic depiction of the selective removal of AuCl4− and its precipitation as solid gold from e-w...
Beilstein J. Org. Chem. 2025, 21, 999–1009, doi:10.3762/bjoc.21.81
Graphical Abstract
Figure 1: Reactivity of enamides and enamide cyclizations.
Scheme 1: Total synthesis of (−)-dihydrolycopodine and (−)-lycopodine.
Scheme 2: Collective total synthesis of fawcettimine-type alkaloids.
Scheme 3: Total syntheses of cephalotaxine and cephalezomine H.
Scheme 4: Collective total syntheses of Cephalotaxus alkaloids.
Scheme 5: Asymmetric tandem cyclization/Pictet–Spengler reaction of tertiary enamides.
Scheme 6: Tandem cyclization/Pictet–Spengler reaction for the synthesis of chiral tetracyclic compounds.
Scheme 7: Total synthesis of (−)-cephalocyclidin A.
Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61
Graphical Abstract
Scheme 1: Electrosynthesis of phenanthridine phosphine oxides.
Scheme 2: Electrosynthesis of 1-aminoalkylphosphine oxides.
Scheme 3: Various electrochemical C–P coupling reactions.
Scheme 4: Electrochemical C–P coupling reaction of indolines.
Scheme 5: Electrochemical C–P coupling reaction of ferrocene.
Scheme 6: Electrochemical C–P coupling reaction of acridines with phosphites.
Scheme 7: Electrochemical C–P coupling reaction of alkenes.
Scheme 8: Electrochemical C–P coupling reaction of arenes in a flow system.
Scheme 9: Electrochemical C–P coupling reaction of heteroarenes.
Scheme 10: Electrochemical C–P coupling reaction of thiazoles.
Scheme 11: Electrochemical C–P coupling reaction of indole derivatives.
Scheme 12: Electrosynthesis of 1-amino phosphonates.
Scheme 13: Electrochemical C–P coupling reaction of aryl and vinyl bromides.
Scheme 14: Electrochemical C–P coupling reaction of phenylpyridine with dialkyl phosphonates in the presence o...
Scheme 15: Electrochemical P–C bond formation of amides.
Scheme 16: Electrochemical synthesis of α-hydroxy phosphine oxides.
Scheme 17: Electrochemical synthesis of π-conjugated phosphonium salts.
Scheme 18: Electrochemical phosphorylation of indoles.
Scheme 19: Electrochemical synthesis of phosphorylated propargyl alcohols.
Scheme 20: Electrochemical synthesis of phosphoramidates.
Scheme 21: Electrochemical reaction of carbazole with diphenylphosphine.
Scheme 22: Electrochemical P–N coupling of carbazole with phosphine oxides.
Scheme 23: Electrochemical P–N coupling of indoles with a trialkyl phosphite.
Scheme 24: Electrochemical synthesis of iminophosphoranes.
Scheme 25: Electrochemical P–O coupling of phenols with dialkyl phosphonate.
Scheme 26: Electrochemical P–O coupling of alcohols with diphenylphosphine.
Scheme 27: Electrochemical P–S coupling of thiols with dialkylphosphines.
Scheme 28: Electrochemical thiophosphorylation of indolizines.
Scheme 29: Electrosynthesis of S-heteroaryl phosphorothioates.
Scheme 30: Electrochemical phosphorylation reactions.
Scheme 31: Electrochemical P–Se formation.
Scheme 32: Electrochemical selenation/halogenation of alkynyl phosphonates.
Scheme 33: Electrochemical enantioselective aryl C–H bond activation.
Beilstein J. Org. Chem. 2025, 21, 630–638, doi:10.3762/bjoc.21.50
Graphical Abstract
Figure 1: Selected examples of α,α-disubstituted cyclic amino acids in drug design.
Figure 2: Electrochemical decarboxylative amination reactions.
Scheme 1: Preparation of malonic acid monoester 9a.
Figure 3: A) Cyclic voltammograms of 6a and 9a at 3 mM and 6 mM concentration, respectively, in 5:1 MeCN/H2O ...
Scheme 2: Electrolysis of acid 9d in deuterated solvents.
Figure 4: Plausible mechanism for formation of pyrrolidine 6a and hemiaminal 10a.
Scheme 3: Scope of the decarboxylative amidation. aStainless-steel cathode; bgraphite cathode; cyield determi...
Scheme 4: Synthetic modifications of 2-aminoproline derivatives 6.
Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22
Graphical Abstract
Figure 1: Influence of the metal center M (Fe, Ru, Os) on the position of the MLCT and MC (metal-centered) ab...
Scheme 1: Red-light-mediated ring-closing metathesis through activation of a ruthenium catalyst by an osmium ...
Scheme 2: Photocatalyzed polymerization of dicylopentadiene mediated with red or blue light.
Figure 2: Comparison between [Ru(bpy)3]2+ and [Os(tpy)2]2+ in a photocatalyzed trifluoromethylation reaction:...
Scheme 3: Red-light photocatalyzed C–N cross-coupling reaction by T. Rovis et al. (SET = single-electron tran...
Figure 3: Red-light-mediated aryl oxidative addition with a bismuthinidene complex.
Scheme 4: Red-light-mediated reduction of aryl derivatives by O. S. Wenger et al. (PC = photocatalyst, anh = ...
Scheme 5: Red-light-mediated aryl halides reduction with an isoelectronic chromium complex (TDAE = tetrakis(d...
Scheme 6: Red-light-photocatalyzed trifluoromethylation of styrene derivatives with Umemoto’s reagent and a p...
Scheme 7: Red-light-mediated energy transfer for the cross-dehydrogenative coupling of N-phenyltetrahydroisoq...
Scheme 8: Red-light-mediated oxidative cyanation of tertiary amines with a phthalocyanin zinc complex.
Scheme 9: Formation of dialins and tetralins via a red-light-photocatalyzed reductive decarboxylation mediate...
Scheme 10: Oxidation of β-citronellol (28) via energy transfer mediated by a red-light activable silicon phtha...
Scheme 11: Formation of alcohol derivatives 32 from boron compounds 31 using chlorophyll (chl) as a red-light-...
Scheme 12: Red-light-driven reductive dehalogenation of α-halo ketones mediated by a thiaporphyrin photocataly...
Figure 4: Photoinduced electron transfer-reversible addition-fragmentation chain transfer polymerization medi...
Figure 5: Recent examples of red-light-mediated photocatalytic reactions with traditional organic dyes.
Figure 6: Squaraine photocatalysts used by Goddard et al. and aza-Henry reaction with squaraine-based photoca...
Figure 7: Reactions described by Goddard et al. involving 40 as the photocatalyst.
Figure 8: Various structures of squaraine derivatives used to initiate photopolymerizations.
Figure 9: Naturally occurring cyanins.
Figure 10: Influence of the structure on the photophysical properties of a cyanin dye.
Figure 11: NIR-light-mediated aza-Henry reaction photocatalyzed by 46.
Scheme 13: Photocatalyzed arylboronic acids oxidation by 46.
Figure 12: Cyanin structures synthetized and characterized by Goddard et al. (redox potentials given against s...
Figure 13: N,N′-Di-n-propyl-1,13-dimethoxyquinacridinium (55) with its redox potentials at its ground state an...
Scheme 14: Dual catalyzed C(sp2)–H arylation of 57 using DMQA 55 as the red-light-absorbing photocatalyst.
Scheme 15: Red-light-mediated aerobic oxidation of arylboronic acids 59 into phenols 60 via the use of DMQA as...
Figure 14: Red-light-photocatalyzed reactions proposed by Gianetti et al. using DMQA as the photocatalyst.
Scheme 16: Simultaneous release of NO and production of superoxide (O2•−) and their combination yielding the p...
Figure 15: Palladium porphyrin complex as the photoredox catalyst and the NO releasing substrate are linked in...
Scheme 17: Uncaging of compound 69 which is a microtubule depolymerizing agent using near IR irradiation. The ...
Scheme 18: Photochemical uncaging of drugs protected with a phenylboronic acid derivative using near IR irradi...
Scheme 19: Photoredox catalytical generation of aminyl radicals with near IR irradiation for the transfer of b...
Scheme 20: Photoredox catalytical fluoroalkylation of tryptophan moieties.
Figure 16: Simultaneous absorption of two photons of infrared light of low energy enables electronic excitatio...
Scheme 21: Uncaging Ca2+ ions using two-photon excitation with near infrared light.
Beilstein J. Org. Chem. 2025, 21, 1–7, doi:10.3762/bjoc.21.1
Graphical Abstract
Figure 1: Structures of compounds 1–3 and the polycyclic skeleton of 1 as mapped on a carbon schwarzite unit ...
Scheme 1: a) Synthesis of 1; b) reactions of 1; c) synthesis of 3.
Figure 2: (a) Structures of 1 in the colorless crystal; (b) structures of (P,M,P)-1 in the yellow crystal. (C...
Figure 3: Structure of (M,P,M)-3 in the crystal of 3·CH2Cl2 (carbon and oxygen atoms are shown as grey and re...
Figure 4: UV–vis absorption spectrum (black line) and emission spectrum (blue line, excited at 400 nm) of com...
Beilstein J. Org. Chem. 2024, 20, 2708–2719, doi:10.3762/bjoc.20.228
Graphical Abstract
Figure 1: Synthesis of uracil-based alkynes and aryl structures [51,62-65].
Figure 2: Structures of uracil derivatives A, B, and C.
Scheme 1: Strategy for the synthesis of the cyclised product 5. Conditions: i) Br2 (2 equiv), Ac2O (1.5 equiv...
Scheme 2: Synthesis and isolated yields of 1,3-dimethyl-5-aryl-6-[2-(aryl)ethynyl]uracils 4a–i. Reaction cond...
Scheme 3: Scope and isolated yields of the synthesis of 5. Reaction conditions: 4 (1 equiv), p-TsOH·H2O (20 e...
Scheme 4: Proposed reaction mechanism of the cyclisation with N,N-dimethylanilino functional groups.
Figure 3: UV–vis absorption (left) and emission (right, λex = 400 nm) spectra of 5a, 5d, 5f, 5g, 5h, and 5i i...
Beilstein J. Org. Chem. 2024, 20, 2608–2634, doi:10.3762/bjoc.20.220
Graphical Abstract
Figure 1: Hierarchical assembly occurring across length scales. Molecular interactions result in fibres which...
Figure 2: Three-dimensional CLSM image of a multicomponent supramolecular structure. The three-dimensional CL...
Figure 3: AFM images of air-dried aqueous Fmoc-FF, Fmoc-S, and 1:1 Fmoc-FF:Fmoc-S solutions. Figure 3 was reprinted f...
Figure 4: (a) 3D CLSM images of macroscopically a self-sorting gel network, where all fibres were stained gre...
Figure 5: (a) 3D AFM topographic image of dried elastin fibre. (b) Indicative height and diameter profile plo...
Figure 6: The nano-to-micro imaging range of SEM and TEM [30]. Cartoons represent the nanoparticles, pores, nanow...
Figure 7: Cartoon of artifacts caused by blotting and thinning. a) Alignment of threadlike micelles (left) [32] a...
Figure 8: (a) Chemical structures of monomer compounds and a schematic of the resulting chiral helical struct...
Figure 9: Commonly observed entanglements of urea-based supramolecular helices. (a) Double helix, (b) quadrup...
Figure 10: (a) SEM image of a single three-stranded braid showing a defect in which the braid separates into s...
Figure 11: Visualization of individual atoms at 1.25 Å resolution. Three apoferritin residues are shown at hig...
Figure 12: Cartoon of a general small-angle scattering setup.
Figure 13: (a) SAXS data and fits for solution in H2O (open symbols) and D2O (closed symbols). Cryo-TEM data f...
Figure 14: (a) A cartoon illustrating the orientation phases caused by shear alignment of WLMs. (b) Rheologica...
Figure 15: (a) Chemical structure of 2NapFF and (b) a cartoon cross-section of the hollow cylinder structure f...
Figure 16: Length scales of scattering and imaging techniques [16,54,55].
Figure 17: A schematic of a hydrogel network showing the significance of various parameters extracted from SAN...
Figure 18: The morphologies of a co-assembled complex dependent on the solvent composition. Figure 18 is from [89] and was ...
Figure 19: Allowed and forbidden crossings of entangled helices. Figure 19 is from [44] and was adapted by permission from ...
Figure 20: (a) Cryo-TEM density map of self-assembled (ʟ,ʟ)-2NapFF. (b) Computational model fit to cryo-TEM ma...
Figure 21: Map showing an incomplete list of global scientific centres providing access to (a) cryo-EM in red ...
Figure 22: SANS at a range of times. Solid lines are fits to a hollow cylinder model (T = 114 min and T = 202 ...
Figure 23: SAXS data of 5 mg/mL alanine-functionalised perylene bisimide (PBI-A) in 20 v/v % MeOH at pH (a) 2;...
Figure 24: Cryo-TEM sample prepared using plunge freezing in liquid nitrogen slush and sublimed for 30 minutes...
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, 1988–2004, doi:10.3762/bjoc.20.175
Graphical Abstract
Scheme 1: Synthesis of triazolopyridinium salts [34-36].
Scheme 2: Synthesis of pyrazoles [37].
Scheme 3: Synthesis of indazoles from ketone-derived hydrazones [38].
Scheme 4: Intramolecular C(sp2)–H functionalization of aldehyde-derived N-(2-pyridinyl)hydrazones for the syn...
Scheme 5: Synthesis of pyrazolo[4,3-c]quinoline derivatives [40].
Scheme 6: Synthesis of 1,3,4-oxadiazoles and Δ3-1,3,4-oxadiazolines [41].
Scheme 7: Synthesis of 1,3,4-oxadiazoles [43].
Scheme 8: Synthesis of 2-(1,3,4-oxadiazol-2-yl)anilines [44].
Scheme 9: Synthesis of fused s-triazolo perchlorates [45].
Scheme 10: Synthesis of 1-aryl and 1,5-disubstitued 1,2,4-triazoles [49].
Scheme 11: Synthesis of 1,3,5-trisubstituted 1,2,4-triazoles [50].
Scheme 12: Alternative synthesis of 1,3,5-trisubstituted 1,2,4-triazoles [51].
Scheme 13: Synthesis of 5-amino 1,2,4-triazoles [55].
Scheme 14: Synthesis of 1-arylpyrazolines [58].
Scheme 15: Synthesis of 3‑aminopyrazoles [60].
Scheme 16: Synthesis of [1,2,4]triazolo[4,3-a]quinolines [61].·
Scheme 17: Synthesis of 1,2,3-thiadiazoles [64].
Scheme 18: Synthesis of 5-thioxo-1,2,4-triazolium inner salts [65].
Scheme 19: Synthesis of 1-aminotetrazoles [66].
Scheme 20: C(sp2)–H functionalization of aldehyde-derived hydrazones: general mechanisms.
Scheme 21: C(sp2)–H functionalization of benzaldehyde diphenyl hydrazone [68,69].
Scheme 22: Phosphorylation of aldehyde-derived hydrazones [70].
Scheme 23: Azolation of aldehyde-derived hydrazones [72].
Scheme 24: Thiocyanation of benzaldehyde-derived hydrazone 122 [73].
Scheme 25: Sulfonylation of aromatic aldehyde-derived hydrazones [74].
Scheme 26: Trifluoromethylation of aromatic aldehyde-derived hydrazones [76].
Scheme 27: Electrooxidation of benzophenone hydrazones [77].
Scheme 28: Electrooxidative coupling of benzophenone hydrazones and alkenes [77].
Scheme 29: Electrosynthesis of α-diazoketones [78].
Scheme 30: Electrosynthesis of stable diazo compounds [80].
Scheme 31: Photoelectrochemical synthesis of alkenes through in situ generation of diazo compounds [81].
Scheme 32: Synthesis of nitriles [82].
Scheme 33: Electrochemical oxidation of ketone-derived NH-allylhydrazone [83].
Beilstein J. Org. Chem. 2024, 20, 1900–1905, doi:10.3762/bjoc.20.165
Graphical Abstract
Scheme 1: Radical and ionic intramolecular cyclizations.
Scheme 2: Electrochemical and photochemical aza-Wacker cyclizations.
Scheme 3: Scope of electrochemical aza-Wacker cyclization. Reaction conditions: the alkene (0.20 mmol), Bu4NO...
Scheme 4: Mechanistic studies of aza-Wacker cyclization. A: Electrochemical (Bu4NOTf in CH3CN/1,2-DCE), B: no...
Figure 1: Cyclic voltammograms for aryl sulfonamides.
Beilstein J. Org. Chem. 2024, 20, 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, 1713–1745, doi:10.3762/bjoc.20.152
Graphical Abstract
Figure 1: Steroidal spiro heterocycles with remarkable pharmacological activity.
Scheme 1: Synthesis of the spirooxetanone 2. a) t-BuOK, THF, rt, 16%.
Scheme 2: Synthesis of the 17-spirooxetane derivative 7. a) HC≡C(CH2)2CH2OTBDPS, n-BuLi, THF, BF3·Et2O, −78 °...
Scheme 3: Pd-catalyzed carbonylation of steroidal alkynols to produce α-methylene-β-lactones at C-3 and C-17 ...
Scheme 4: Catalyst-free protocol to obtain functionalized spiro-lactones by an intramolecular C–H insertion. ...
Scheme 5: One-pot procedure from dienamides to spiro-β-lactams. a) 1. Ac2O, DMAP, Et3N, CH2Cl2, 2. malononitr...
Scheme 6: Spiro-γ-lactone 20 afforded from 7α-alkanamidoestrone derivative 17. a) HC≡CCH2OTHP, n-BuLi, THF, –...
Scheme 7: Synthesis of the 17-spiro-γ-lactone 23, a key intermediate to obtain spironolactone. a) Ethyl propi...
Scheme 8: Synthetic pathway to obtain 17-spirodihydrofuran-3(2H)-ones from 17-oxosteroids. a) 1-Methoxypropa-...
Scheme 9: One-pot procedure to obtain 17-spiro-2H-furan-3-one compounds. a) NaH, diethyl oxalate, benzene, rt...
Scheme 10: Synthesis of 17-spiro-2H-furan-3-one derivatives. a) RCH=NOH, N-chlorosuccinimide/CHCl3, 99%; b) H2...
Scheme 11: Intramolecular condensation of a γ-acetoxy-β-ketoester to synthesize spirofuranone 37. a) (CH3CN)2P...
Scheme 12: Synthesis of spiro 2,5-dihydrofuran derivatives. a) Allyl bromide, DMF, NaH, 0 °C to rt, 93%; b) G-...
Scheme 13: First reported synthesis of C-16 dispiropyrrolidine derivatives. a) Sarcosine, isatin, MeOH, reflux...
Scheme 14: Cycloadducts 47 with antiproliferative activity against human cancer cell lines. a) 1,4-Dioxane–MeO...
Scheme 15: Spiropyrrolidine compounds generated from (E)-16-arylidene steroids and different ylides. a) Acenap...
Scheme 16: 3-Spiropyrrolidines 52a–c obtained from ketones 50a–c. a) p-Toluenesulfonyl hydrazide, MeOH, rt; b)...
Scheme 17: 16-Spiropyrazolines from 16-methylene-13α-estrone derivatives. a) AgOAc, toluene, rt, 78–81%.
Scheme 18: 6-Spiroimidazolines 57 synthesized by a one-pot multicomponent reaction. a) R3-NC, T3P®, DMSO, 70 °...
Scheme 19: Synthesis of spiro-1,3-oxazolines 60, tested as progesterone receptor antagonist agents. a) CF3COCF3...
Scheme 20: Synthesis of spiro-1,3-oxazolidin-2-ones 63 and 66a,b. a) RNH2, EtOH, 70 °C, 70–90%; b) (CCl3O)2CO,...
Scheme 21: Formation of spiro 1,3-oxazolidin-2-one and spiro 2-substituted amino-4,5-dihydro-1,3-oxazoles from ...
Scheme 22: Synthesis of diastereomeric spiroisoxazolines 74 and 75. a) Ar-C(Cl)=N-OH, DIPEA, toluene, rt, 74 (...
Scheme 23: Spiro 1,3-thiazolidine derivatives 77–79 obtained from 2α-bromo-5α-cholestan-3-one 76. a) 2-aminoet...
Scheme 24: Method for the preparation of derivative 83. a) Benzaldehyde, MeOH, reflux, 77%; b) thioglycolic ac...
Scheme 25: Synthesis of spiro 1,3-thiazolidin-4-one derivatives from steroidal ketones. a) Aniline, EtOH, refl...
Scheme 26: Synthesis of spiro N-aryl-1,3-thiazolidin-4-one derivatives 91 and 92. a) Sulfanilamide, DMF, reflu...
Scheme 27: 1,2,4-Trithiolane dimers 94a–e selectively obtained from carbonyl derivatives. a) LR, CH2Cl2, reflu...
Scheme 28: Spiro 1,2,4-triazolidin-3-ones synthesized from semicarbazones. a) H2O2, CHCl3, 0 °C, 82–85%.
Scheme 29: Steroidal spiro-1,3,4-oxadiazoline 99 obtained in two steps from cholest-5-en-3-one (97). a) NH2NHC...
Scheme 30: Synthesis of spiro-1,3,4-thiadiazoline 101 by cyclization and diacetylation of thiosemicarbazone 100...
Scheme 31: Mono- and bis(1,3,4-thiadiazolines) obtained from estrane and androstane derivatives. a) H2NCSNHNH2...
Scheme 32: Different reaction conditions to synthesize spiro-1,3,2-oxathiaphospholanes 108 and 109.
Scheme 33: Spiro-δ-lactones derived from ADT and epi-ADT as inhibitors of 17β-HSDs. a) CH≡C(CH2)2OTHP, n-BuLi,...
Scheme 34: Spiro-δ-lactams 123a,b obtained in a five-step reaction sequence. a) (R)-(+)-tert-butylsulfinamide,...
Scheme 35: Steroid-coumarin conjugates as fluorescent DHT analogues to study 17-oxidoreductases for androgen m...
Scheme 36: 17-Spiro estradiolmorpholinones 130 bearing two types of molecular diversity. a) ʟ- or ᴅ-amino acid...
Scheme 37: Steroidal spiromorpholinones as inhibitors of enzyme 17β-HSD3. a) Methyl ester of ʟ- or ᴅ-leucine, ...
Scheme 38: Steroidal spiro-morpholin-3-ones achieved by N-alkylation or N-acylation of amino diols 141, follow...
Scheme 39: Straightforward method to synthesize a spiromorpholinone derivative from estrone. a) BnBr, K2CO3, CH...
Scheme 40: Pyrazolo[4,3-e][1,2,4]-triazine derivatives 152–154. a) 4-Aminoantipyrine, EtOH/DMF, reflux, 82%; b...
Scheme 41: One-pot procedure to synthesize spiro-1,3,4-thiadiazine derivatives. a) NH2NHCSCONHR, H2SO4, dioxan...
Scheme 42: 1,2,4-Trioxanes with antimalarial activity. a) 1. O2, methylene blue, CH3CN, 500 W tungsten halogen...
Scheme 43: Tetraoxanes 167 and 168 synthesized from ketones 163, 165 and 166. a) NaOH, iPrOH/H2O, 80 °C, 93%; ...
Scheme 44: 1,2,4,5-Tetraoxanes bearing a steroidal moiety and a cycloalkane. a) 30% H2O2/CH2Cl2/CH3CN, HCl, rt...
Scheme 45: Spiro-1,3,2-dioxaphosphorinanes obtained from estrone derivatives. a) KBH4, MeOH, THF or CH2Cl2; b)...
Scheme 46: Synthesis of steroidal spiro-ε-lactone 183. a) 1. Jones reagent, acetone, 0 °C to rt, 2. ClCOCOCl, ...
Scheme 47: Synthesis of spiro-2,3,4,7-tetrahydrooxepines 185 and 187 derived from mestranol and lynestrenol (38...
Beilstein J. Org. Chem. 2024, 20, 1278–1285, doi:10.3762/bjoc.20.110
Graphical Abstract
Scheme 1: Overview of the synthesis of compounds 1–63.
Figure 1: Temperature-dependent viscosity measurement of NTf2− TAAILs 37–63 with a butyl chain and different ...
Figure 2: Conductivity of NTf2− TAAILs 37–63 measured at 25 °C. Compounds 48, 51, and 54 are excluded because...
Figure 3: Conductivity of NTf2− TAAILs with a butyl chain plotted against their viscosity at 25 °C.
Figure 4: Linear sweep voltammetry of NTf2− TAAILs with a butyl chain and different aryl substituents R. Blac...
Figure 5: Structures of the imidazolium cations obtained by DFT calculations (B3LYP/6-311++G (d,p)). The elec...
Beilstein J. Org. Chem. 2024, 20, 1270–1277, doi:10.3762/bjoc.20.109
Graphical Abstract
Figure 1: Characterization data. (a) FTIR spectra of t-Bu-FIDO and t-Bu-FIDS. (b) UV–vis spectra of fullerene...
Figure 2: Single-crystal structure of t-Bu-FIDS. (a) The π–π distance between two molecules. (b) Crystal pack...
Figure 3: Cyclic voltammograms of fullerene derivatives in o-DCB solution containing Bu4N+(CF3SO2)2N− (0.1 M)...
Figure 4: J–V curves of BHJ OPV devices. (a) ITO/ZnO/fullerene:P3HT (1:1, w/w)/PEDOT:PSS/Ag. (b) ITO/ZnO/full...
Beilstein J. Org. Chem. 2024, 20, 1179–1188, doi:10.3762/bjoc.20.100
Graphical Abstract
Figure 1: Positional notation of 6,6-bonds in a mono-adduct of C60 with the first addition site indicated usi...
Scheme 1: Synthesis of silylene adducts 2 and 3.
Figure 2: Absorption spectrum of 3 in CH2Cl2.
Figure 3: 500 MHz 1H NMR spectrum of 3 in CDCl3/CS2 3:1.
Figure 4: 125 MHz 13C NMR spectrum of 3 in CDCl3/CS2 3:1. The signals of sp2 carbons of C60 and quaternary ca...
Figure 5: ORTEP drawing of 3 showing thermal ellipsoids at the 50% probability level at 100 K. Hydrogen atoms...
Figure 6: (a) Partial structures of isomers of Dip2SiC60. (b) Optimized structures of 2a and 2c. Hydrogen ato...
Figure 7: Optimized structures of 3cis-2, 3cis-3, 3e, 3trans-1, 3trans-2, 3trans-3, and 3trans-4. Values in p...
Figure 8: (a) LUMO and (b) HOMO of 2a calculated at the B3LYP/6-31G(d) level. Hydrogen atoms are omitted for ...
Figure 9: Cyclic voltammograms (CV) and differential pulse voltammograms (DPV) of 3 in o-dichlorobenzene cont...
Beilstein J. Org. Chem. 2024, 20, 1037–1052, doi:10.3762/bjoc.20.92
Graphical Abstract
Figure 1: Chemical structures of H-bonding N-heteroacenes synthesized by Miao et al. and Bunz et al. (a) [22,23]. Pr...
Scheme 1: Synthesis of dicyanopyrazinoquinoxaline derivatives 1a–7a.
Scheme 2: Synthesis of bis-alkoxy-substituted π-conjugated phenanthrolines 16a, 16b, 16c, and 16d.
Scheme 3: An alternative synthetic route to access 7a.
Scheme 4: Synthesis of DPQDs 1b–7b from their corresponding DCPQs 1a–7a. *THF/H2O/1,4-dioxane (4:5:1). **in s...
Figure 2: TGA of 1a–6a (a) and 1b–7b (b) obtained at 10 °C/min under nitrogen.
Figure 3: Absorption spectra (20 μM) for a) DCPQs 1a–6a and b) DPQDs 1b–7b in dimethyl sulfoxide.
Figure 4: Calculated HOMO (below) and LUMO (above) energies by DFT analysis (B3LYP/6-31+G* level of theory), ...
Figure 5: Calculated HOMO (below) and LUMO (above) energies by DFT analysis (B3LYP/6-31+G* level of theory), ...
Figure 6: Asymmetric unit of DPQD 2b with important bond lengths highlighted (a). Torsion angles of 4.33° and...
Beilstein J. Org. Chem. 2024, 20, 787–814, doi:10.3762/bjoc.20.72
Graphical Abstract
Scheme 1: Classes of hydrochlorination reactions discussed in this review.
Figure 1: Mayr’s nucleophilicity parameters for several alkenes. References for each compound can be consulte...
Figure 2: Hydride affinities relating to the reactivity of the corresponding alkene towards hydrochlorination....
Scheme 2: Distinction of polar hydrochlorination reactions.
Scheme 3: Reactions of styrenes with HCl gas or HCl solutions.
Figure 3: Normal temperature dependence for the hydrochlorination of (Z)-but-2-ene.
Figure 4: Pentane slows down the hydrochlorination of 11.
Scheme 4: Recently reported hydrochlorinations of styrenes with HCl gas or HCl solutions.
Scheme 5: Hydrochlorination reactions with di- and trisubstituted alkenes.
Scheme 6: Hydrochlorination of fatty acids with liquified HCl.
Scheme 7: Hydrochlorination with HCl/DMPU solutions.
Scheme 8: Hydrochlorination with HCl generated from EtOH and AcCl.
Scheme 9: Hydrochlorination with HCl generated from H2O and TMSCl.
Scheme 10: Regioisomeric mixtures of chlorooctanes as a result of hydride shifts.
Scheme 11: Regioisomeric mixtures of products as a result of methyl shifts.
Scheme 12: Applications of the Kropp procedure on a preparative scale.
Scheme 13: Curious example of polar anti-Markovnikov hydrochlorination.
Scheme 14: Unexpected and expected hydrochlorinations with AlCl3.
Figure 5: Ex situ-generated HCl gas and in situ application for the hydrochlorination of activated alkenes (*...
Scheme 15: HCl generated by Grob fragmentation of 92.
Scheme 16: Formation of chlorophosphonium complex 104 and the reaction thereof with H2O.
Scheme 17: Snyder’s hydrochlorination with stoichiometric amounts of complex 104 or 108.
Scheme 18: In situ generation of HCl by mixing of MsOH with CaCl2.
Scheme 19: First hydrochlorination of alkenes using hydrochloric acid.
Scheme 20: Visible-light-promoted hydrochlorination.
Scheme 21: Silica gel-promoted hydrochlorination of alkenes with hydrochloric acid.
Scheme 22: Hydrochlorination with hydrochloric acid promoted by acetic acid or iron trichloride.
Figure 6: Metal hydride hydrogen atom transfer reactions vs cationic reactions; BDE (bond-dissociation energy...
Scheme 23: Carreira’s first report on radical hydrochlorinations of alkenes.
Figure 7: Mechanism for the cobalt hydride hydrogen atom transfer reaction reported by Carreira.
Scheme 24: Radical “hydrogenation” of alkenes; competing chlorination reactions.
Scheme 25: Bogers iron-catalyzed radical hydrochlorination.
Scheme 26: Hydrochlorination instead of hydrogenation product.
Scheme 27: Optimization of the Boger protocol by researchers from Merck [88,89].
Figure 8: Proposed mechanism for anti-Markovnikov hydrochlorination by Nicewicz.
Scheme 28: anti-Markovnikov hydrochlorinations as reported by Nicewicz.
Figure 9: Mechanism for anti-Markovnikov hydrochlorination according to Ritter.
Scheme 29: anti-Markovnikov hydrochlorinations as reported by Nicewicz; rr (regioisomeric ratio) corresponds t...
Scheme 30: anti-Markovnikov hydrochlorinations as reported by Liu.
Beilstein J. Org. Chem. 2024, 20, 721–733, doi:10.3762/bjoc.20.66
Graphical Abstract
Scheme 1: Brief introduction of thioesterase (TE) domain. (a) NRPS and PKS assembly lines. (b) Mechanism of T...
Scheme 2: Chemoenzymatic synthesis of tyrocidine A and its analogs. (a) First-gen chemoenzymatic synthesis of...
Scheme 3: Representative examples of NAC-activated thioesters-mediated biocatalytic macrolactamization.
Scheme 4: Chemoenzymatic synthesis of CDA, daptomycin and their analogs. (a) Biocatalytic macrocyclization of...
Scheme 5: Chemoenzymatic synthesis of surugamide B and related natural products. (a) Three synthetic strategi...
Scheme 6: Chemoenzymatic synthesis of the pikromycins. (a) Macrocyclization of 10-deoxymethynolide catalyzed ...
Scheme 7: Chemoenzymatic synthesis of the juevnimicins.
Scheme 8: Chemoenzymatic synthesis of the cryptophycins.
Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45
Graphical Abstract
Figure 1: Principle of switchable molecular tweezers.
Figure 2: Principle of pH-switchable molecular tweezers 1 [19].
Figure 3: a) pH-Switchable tweezers 2 substituted with alkyl chains as switchable lipids. b) Schematic depict...
Figure 4: Modification of spectral properties of 3 by controlled induction of Pt–Pt interactions.
Figure 5: Conformational switching of di(hydroxyphenyl)pyrimidine-based tweezer 4 upon alkylation or fluoride...
Figure 6: Hydrazone-based pH-responsive tweezers 5 for mesogenic modulation.
Figure 7: pH-Switchable molecular tweezers 6 bearing acridinium moieties.
Figure 8: a) Terpyridine and pyridine-hydrazone-pyridine analogs molecular tweezers and b) extended pyridine ...
Figure 9: Terpyridine-based molecular tweezers with M–salphen arms and their field of application. Figure 9 was adapt...
Figure 10: a) Terpyridine-based molecular tweezers for diphosphate recognition [48]; b) bishelicene chiroptical te...
Figure 11: Terpyridine-based molecular tweezers with allosteric cooperative binding.
Figure 12: Terpyridine-based molecular tweezers presenting closed by default conformation.
Figure 13: Pyridine-pyrimidine-pyridine-based molecular tweezers.
Figure 14: Coordination-responsive molecular tweezers based on nitrogen-containing ligands.
Figure 15: Molecular tweezers exploiting the remote bipyridine or pyridine binding to trigger the conformation...
Figure 16: Bipyridine-based molecular tweezers exploiting the direct s-trans to s-cis-switching for a) anion b...
Figure 17: a) Podand-based molecular tweezers [66,67]. b) Application of tweezers 32 for the catalytic allosteric reg...
Figure 18: Anion-triggered molecular tweezers based on calix[4]pyrrole.
Figure 19: Anion-triggered molecular tweezers.
Figure 20: a) Principle of the weak link approach (WLA) developed by Mirkin and its application to b) symmetri...
Figure 21: Molecular tweezers as allosteric catalyst in asymmetric epoxide opening [80].
Figure 22: Allosteric regulation of catalytic activity in ring-opening polymerization with double tweezers 41.
Figure 23: a) Conformational switching of 42 by intramolecular –S–S– bridge formation. b) Shift of conformatio...
Figure 24: a) Redox-active glycoluril-TTF tweezers 44. b) Mechanism of stepwise oxidation of said tweezers wit...
Figure 25: Mechanism of formation of the mixed-valence dimers of tweezers 45.
Figure 26: Mechanism of carbohydrate liberation upon redox-mediated conformation switching of 46.
Figure 27: a) The encapsulation properties of 47 as well as the DCTNF release process from its host–guest comp...
Figure 28: Redox-active bipyridinium-based tweezers. a) With a ferrocenyl hinge 49, b) with a propyl hinge 50 ...
Figure 29: Redox-active calix[4]arene porphyrin molecular tweezers.
Figure 30: a) Mechanism of the three orthogonal stimuli. b) Cubic scheme showing the eight different states of ...
Figure 31: Redox-controlled molecular gripper based on a diquinone resorcin[4]arene.
Figure 32: a) Shinkai's butterfly tweezers and their different host–guest properties depending on the isomer. ...
Figure 33: Cyclam-tethered tweezers and their different host–guest complexes depending on their configuration.
Figure 34: Azobenzene-based catalytic tweezers.
Figure 35: Photoswitchable PIEZO channel mimic.
Figure 36: Stilbene-based porphyrin tweezers for fullerene recognition.
Figure 37: Stiff-stilbene-based tweezers with urea or thiourea functional units for a) anion binding, b) anion...
Figure 38: Feringa’s photoswitchable organocatalyst (a) and different catalyzed reactions with that system (b)....
Figure 39: a) Irie and Takeshita’s thioindigo-based molecular tweezers. b) Family of hemithioindigo-based mole...
Figure 40: Dithienylethylene crown ether-bearing molecular tweezers reported by Irie and co-workers.
Beilstein J. Org. Chem. 2024, 20, 479–496, doi:10.3762/bjoc.20.43
Graphical Abstract
Scheme 1: Proposed mechanism and observation of alkylgold intermediates.
Figure 1: First order alkene decay for urea alkene 1a (0.05 M) hydroamination with [JPhosAu(NCCH3)]SbF6 (5, 2...
Figure 2: Cooperative effect of mixed CD2Cl2/MeOH on alkene 1a → 3a conversion with catalyst 5 (2.5 mol %). E...
Figure 3: Different additive impact on rate of 1a → 3a depending upon catalyst and co-solvent. The data for J...
Figure 4: (a) Schematic for synthesis of [L–Au–L]SbF6 where L = JPhos. (b) Perspective drawing of the cation ...
Figure 5: (a) kobs for reaction of urea 1a (0.05 M) in DCM with catalyst 5 and titrated CH3OH/CH3OD. Data for...
Figure 6: Rate of urea 1a (0.05 M) hydroamination with JPhosAu(NCCH3)SbF6 (2.5 mol %) in CH2Cl2 with 5, 25, a...
Figure 7: Observed rates for the reaction of carbamate 1b (0.03–0.24 M) with JackiephosAuNTf2 (0.0013 M, 6a) ...
Figure 8: Influence of catalyst 5 concentration on rate of 1a (0.05 M in CH2Cl2 with 0, 10 μL MeOH). Error ba...
Scheme 2: Proposed alternate mechanism.
Beilstein J. Org. Chem. 2024, 20, 452–459, doi:10.3762/bjoc.20.40
Graphical Abstract
Scheme 1: Synthesis of 2,3-dibromo-1,1,1,4,4,4-hexafluorobutane (2).
Scheme 2: Synthesis of (E)-butene 3a.
Scheme 3: Isomerization reaction of (E)-butene 3a to (Z)-butene 3b.
Scheme 4: Synthesis of 2-chloro-3-iodo-1,1,1,4,4,4-hexafluorobutane (5).
Scheme 5: Dehydrohalogenation reaction of 2-chloro-3-iodo-1,1,1,4,4,4-hexafluorobutane (5).
Scheme 6: The reaction of silane 8 with I2/KF.
Scheme 7: The reaction of 3a with iPrMgCl and 4-fluorobenzaldehyde (9).
Scheme 8: The reaction of olefin 3a with iPrMgCl.
Scheme 9: The reaction of (E)-butene 3a with BuLi.
Scheme 10: The reaction of allene 11 with bromine.
Scheme 11: The reaction of allene 11 with ICl.
Scheme 12: Synthesis of 2,3-dibromo-2-chloro-1,1,1,4,4,4-hexafluorobutane (16).
Scheme 13: Synthesis of (Z, E)-2-bromo-3-chloro-1,1,1,4,4,4-hexafluorobut-2-enes (17a,b).
Scheme 14: The reaction of olefins 17a,b with BuLi.
Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30
Graphical Abstract
Scheme 1: “Precursor approach” for the synthesis of π-conjugated polycyclic compounds, with the thermally- or...
Scheme 2: Valence isomerization of chalcogen heteropines and subsequent cheletropic extrusion in the case of ...
Scheme 3: Early example of phenanthrene synthesis via a chemically-induced S-extrusion (and concomitant decar...
Scheme 4: Top: Conversion of dinaphthothiepine bisimides 3a,b and their sulfoxide analogues 4a,b into PBIs 6a,...
Figure 1: Top view (a) and side view (b) of the X-ray crystal structure of thiepine 3b showing its bent confo...
Scheme 5: Modular synthetic route towards dinaphthothiepines 3a–f and the corresponding S-oxides 4a–d, incorp...
Scheme 6: Top: Conversion of dithienobenzothiepine monomeric units into dithienonaphthalenes, upon S-extrusio...
Scheme 7: Synthesis of S-doped extended triphenylene derivative 22 from 3-bromothiophene (17) with the therma...
Scheme 8: Top: Synthesis of thermally-stable O-doped HBC 26a. Bottom: Synthesis of S- and Se-based soluble pr...
Scheme 9: Synthesis of dinaphthooxepine bisimide 33 and conversion into PBI 6f by O-extrusion triggered by el...
Figure 2: Cyclic voltammogram of dinaphthooxepine 33, evidencing the irreversibility of the reduction process...
Scheme 10: Top: Early example of 6-membered ring contraction with concomitant S-extrusion leading to dinaphtho...
Scheme 11: Examples of S-extrusion from annelated 1,2-dithiins under photoactivation (top) or thermal activati...
Scheme 12: Synthesis of dibenzo[1,4]dithiapentalene upon photoextrusion of SO2 [78].
Scheme 13: Extrusion of SO in naphthotrithiin-2-oxides for the synthesis of 2,5-dihydrothiophene 1-oxides [79].
Scheme 14: SO-extrusion as a key step in the synthesis of fullerenes (C60 and C70) encapsulating H2 molecules [80,82]....
Scheme 15: Synthesis of diepoxytetracene precursor 56 and its on-surface conversion into tetracene upon O-extr...
Scheme 16: Soluble precursors of hexacene, decacene and dodecacene incorporating 1,4-epoxides in their hydroca...
Scheme 17: Synthesis of tetraepoxide 59 as soluble precursor of decacene [85].
Figure 3: Constant-height STM measurement of decacene on Au(111) using a CO-functionalized tip (sample voltag...