Copper catalysis in organic synthesis
The growth in copper-catalyzed organic reactions is driven by a couple of factors. First, copper chemistry is incredibly diverse. Depending on its oxidation state, this metal can efficiently catalyze reactions involving both one and two-electron mechanisms. Copper coordinates easily to heteroatoms and to π-bonds and is well-known to activate terminal alkynes. The Ullman and Goldberg C–C and C–N cross-coupling reactions were discovered over a century ago and their development has really blossomed over the past twenty years. Second, copper is an earth-abundant metal, making its use more cost effective and more sustainable than precious transition metal catalysts. It is clear from the impact copper catalysis has had on organic synthesis that copper should be considered a first line catalyst for many organic reactions. Further growth in the field is anticipated in the years to come.
See also the Thematic Series:
Transition-metal and organocatalysis in natural product synthesis
Gold catalysis for organic synthesis II
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- Published 14 Aug 2015
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Figure 1: A sampling of propargylamine-derived triazoles with therapeutic effects includes alpha-tetrasubstit...
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Figure 2: A tetrasubstituted carbon bearing an amine (red) can provide 100-fold increase in activity compared...
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Scheme 1: KA2 coupling followed by tandem silyl deprotection and triazole formation.
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Scheme 2: Silyl deprotection/click conditions applied to tert-butylacetylene. An identical yield is observed ...
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Scheme 3: High overall yield of 1,2,3-triazole fully-substituted at the 4-position.
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- Published 19 Oct 2015
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Scheme 1: Generation of iminyl radicals from oxime derivatives.
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Scheme 2: Oxidative generation of iminyl radicals from N–H ketimines.
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Scheme 3: Copper-catalyzed aerobic reactions of in situ generated biaryl N–H ketimines.
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Scheme 4: Copper-catalyzed aerobic C–C bond cleavage reactions of N–H ketimines.
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Scheme 5: Proposed reaction mechanisms for the formation of 3a, 4a and 5a, and the reaction of hydroperoxide 6...
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Scheme 6: Formation of bromoketone 6e.
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Scheme 7: Electrophilic cyanation of Grignard reagents with pivalonitrile (1f).
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Scheme 8: Electrophilic cyanation with pivalonitrile (1e).
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- Published 21 Oct 2015
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Scheme 1: Structures of photoactivable click catalysts 1–3.
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Scheme 2: Syntheses of complexes 1 and 4.
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Figure 1: a) Molecular structure of 4 (a THF molecule present in the unit cell is not shown). Cu, green; C, g...
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Figure 2: Evolution of the UV–vis spectra of deaerated (freeze-pump-thaw degassed, sealed quartz cuvettes) TH...
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Scheme 3: Proposed mechanism for the photoreduction process.
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Figure 3: Evolution of the EPR spectra (X band, 298 K) of solutions of 1 under continuous irradiation (280–40...
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Figure 4: Reaction profiles for the formation of 9 under various illumination conditions: TLC lamp (365 nm) f...
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Scheme 4: Structures, conversions and isolated yields for triazoles 9–17 conducted in D2O in NMR tubes.
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Scheme 5: Preparative scale synthesis of 18 and 19.
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- Published 27 Oct 2015
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Scheme 1: Standard reaction conditions.
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Scheme 2: Formation of aliphatic chiral β-hydroxy nitrile 2g and its subsequent conversion into 4g.
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- Published 03 Nov 2015
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Scheme 1: Examples of ferrocene derived drugs and ligands.
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Scheme 2: Structural types of ferrocene-based polymers.
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Scheme 3: Synthesis of ferrocene-derived alkenes from ferrocene carbaldehyde.
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Scheme 4: Synthesis of ferrocene-derived alkenes from acetylferrocene and 1,1’-diacetylferrocene.
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Figure 1: Typical voltammogramms of vinylferrocenes 7 (blue), 11 (green), 12 (red), anodic region.
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Figure 2: Typical voltammogramms of divinylferrocenes 10 (black), 11 (red), 12 (blue), cathodic region.
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- Published 04 Nov 2015
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Scheme 1: Use of a Chan–Lam reaction for the synthesis of tetrahydroquinolines and potential extension to pyr...
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Scheme 2: Examples of pyridine synthesis from oxime precursors [51,52].
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Scheme 3: Solvent effect on conversion of N-alkenylnitrones to pyridines.
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Scheme 4: Mechanistic experiments.
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- Published 09 Nov 2015
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Scheme 1: Copper-catalyzed C–H bond halogenation of 2-arylpyridine.
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Scheme 2: ortho-Chlorination of 2-arylpridines with acyl chlorides.
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Scheme 3: Copper-catalyzed chlorination of 2-arylpyridines using LiCl.
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Scheme 4: Copper-catalyzed C–H halogenation of 2-arylpyridines using LiX.
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Scheme 5: Copper-mediated selective C–H halogenations of 2-arylpyridine.
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Scheme 6: Copper-catalyzed C–H o-halogenation using removable DG.
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Scheme 7: Copper-catalyzed C–H halogenations using PIP as DG.
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Scheme 8: Copper-catalyzed quinoline C–H chlorination.
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Scheme 9: Copper-catalyzed arene C–H fluorination of benzamides.
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Scheme 10: Copper-catalyzed arene C–H iodination of 1,3-azoles.
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Scheme 11: Copper-catalyzed C–H halogenations of phenols.
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Scheme 12: Proposed mechanism for the C–H halogenation of phenols.
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Scheme 13: Copper-catalyzed halogenation of electron enriched arenes.
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Scheme 14: Copper-catalyzed C–H bromination of arenes.
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Scheme 15: CuI-mediated synthesis of iododibenzo[b,d]furans via C–H functionalization.
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Scheme 16: Cu-Mn spinel oxide-catalyzed phenol and heteroarene halogenation.
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Scheme 17: Copper-catalyzed halogenations of 2-amino-1,3thiazoles.
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Scheme 18: Copper-mediated chlorination and bromination of indolizines.
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Scheme 19: Copper-catalyzed three-component synthesis of bromoindolizines.
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Scheme 20: Copper-mediated C–H halogenation of azacalix[1]arene[3]pyridines.
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Scheme 21: Copper-mediated cascade synthesis of halogenated pyrrolones.
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Scheme 22: Copper-mediated alkene C–H chlorination in spirothienooxindole.
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Scheme 23: Copper-catalyzed remote C–H chlorination of alkyl hydroperoxides.
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Scheme 24: Copper-catalyzed C–H fluorination of alkanes.
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Scheme 25: Copper-catalyzed or mediated C–H halogenations of active C(sp3)-bonds.
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- Letter
- Published 10 Nov 2015
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Scheme 1: Reaction of organozinc compounds.
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Scheme 2: Proposed mechanism.
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- Published 11 Nov 2015
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Scheme 1: Traditional activating mode and oxidative activation mode of free carboxylic acids in amide formati...
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Scheme 2: Substrate scope for catalytic, direct amide formation from carboxylic acids and azoles. Reaction co...
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Scheme 3: Further investigation into the scope of amine.
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Scheme 4: Possible transamidation process.
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Scheme 5: Scope of the amine transamidation from benzimidazole amides. Reaction conditions: benzimidazole ami...
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Scheme 6: Preparative scale of the reaction.
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Scheme 7: Radical scavenger reaction.
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Scheme 8: Control reactions.
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Scheme 9: Proposed mechanism.
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- Published 17 Nov 2015
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Scheme 1: Copper-catalyzed C–H amidation of tertiary amines.
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Scheme 2: Copper-catalyzed C–H amidation and sulfonamidation of tertiary amines.
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Scheme 3: Copper-catalyzed sulfonamidation of allylic C–H bonds.
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Scheme 4: Copper-catalyzed sulfonamidation of benzylic C–H bonds.
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Scheme 5: Copper-catalyzed sulfonamidation of C–H bonds adjacent to oxygen.
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Scheme 6: Copper-catalyzed amidation and sulfonamidation of inactivated alkyl C–H bonds.
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Scheme 7: Copper-catalyzed amidation and sulfonamidation of inactivated alkanes.
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Scheme 8: Copper-catalyzed intramolecular C–H amidation for lactam synthesis.
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Scheme 9: Copper-catalyzed intramolecular C–H amidation for lactam synthesis.
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Scheme 10: Copper-catalyzed amidation/sulfonamidation of aryl C–H bonds.
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Scheme 11: C–H amidation of pyridinylbenzenes and indoles.
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Scheme 12: Mechanism of the Cu-catalyzed C2-amidation of indoles.
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Scheme 13: Copper-catalyzed, 2-phenyl oxazole-assisted C–H amidation of benzamides.
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Scheme 14: DG-assisted amidation/imidation of indole and benzene C–H bonds.
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Scheme 15: Copper-catalyzed C–H amination/amidation of quinoline N-oxides.
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Scheme 16: Copper-catalyzed aldehyde formyl C–H amidation.
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Scheme 17: Copper-catalyzed formamide C–H amidation.
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Scheme 18: Copper-catalyzed sulfonamidation of vinyl C–H bonds.
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Scheme 19: CuCl2-catalyzed amidation/sulfonamidation of alkynyl C–H bonds.
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Scheme 20: Cu(OH)2-catalyzed amidation/sulfonamidation of alkynyl C–H bonds.
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Scheme 21: Sulfonamidation-based cascade reaction for the synthesis of tetrahydrotriazines.
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Scheme 22: Copper-catalyzed cascade reaction for the synthesis of quinazolinones.
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Scheme 23: Copper-catalyzed cascade reactions for the synthesis of fused quinazolinones.
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Scheme 24: Copper-catalyzed synthesis of quinazolinones via methyl C–H bond amidation.
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Scheme 25: Dicumyl peroxide-based cascade synthesis of quinazolinones.
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Scheme 26: Copper-catalyzed cascade reactions for the synthesis of indolinones.
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- Review
- Published 23 Nov 2015
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Scheme 1: Reactivity of nitronate anions towards alkyl electrophiles.
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Scheme 2: Ligands tested in the alkylation of nitroalkanes with alkyl halides. aNaOt-Bu as base, hexanes as s...
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Scheme 3: Scope of the copper-catalyzed nitroalkane benzylation.
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Scheme 4: Application of the nitro-alkylation reaction to the synthesis of phentermine.
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Scheme 5: Possible mechanism of the thermal redox process.
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Scheme 6: Scope of the reaction of nitroalkanes with α-bromocarbonyls.
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Scheme 7: Synthesis of highly congested β-amino acids.
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Scheme 8: Copper-catalyzed alkenylation reactions.
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Scheme 9: Proposed mechanism of the copper-catalyzed alkenylation reaction.
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Scheme 10: Scope of the copper-catalyzed alkenylation of tertiary electrophiles.
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Scheme 11: Scope of the exo-methylene styrene synthesis.
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Scheme 12: Phenol-directed synthesis of Z-alkenes.
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Scheme 13: Scope of the phenol-directed Z-alkene synthesis.
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Scheme 14: Rationale for the formal [3 + 2] cycloaddition.
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Scheme 15: Scope of the formal [3 + 2] cycloaddition.
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Scheme 16: Benzylation of styrenes using copper catalysis.
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Scheme 17: Copper-catalyzed carboiodination of alkynes.
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Scheme 18: Copper-catalyzed trans-carbohalogenation of alkynes. aNaI (2 equiv) was added.
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- Published 24 Nov 2015
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Figure 1: Diamines and polyamines studied in Cu(I)-catalyzed amination reactions.
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Scheme 1: N,N’-Diarylation of the diamines 1 and 2.
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Scheme 2: Arylation of the diamines 1 and 2.
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Scheme 3: Arylation of the diamines 3 and 4.
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Scheme 4: Arylation of the diamines 1, 3, 4 with 2-fluoroiodobenzene.
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Scheme 5: Arylation of the triamines 5 and 6.
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Scheme 6: Arylation of the tetraamines 7 and 8.
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- Published 30 Nov 2015
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Scheme 1: CuI-catalyzed synthesis of benzimidazo[1,2-c]quinazolines 4 by intramolecular N-arylation of bromo-...
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Scheme 2: Cu-catalyzed reaction of o-cyanoaniline (1a), benzonitrile (1g) and di-(o-bromophenyl)iodonium salt ...
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Scheme 3: Acid-promoted ring-opening reaction from quinazoline 4c to 5.
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Figure 1: ORTEP drawing of 5, [C20H16F2N4O]·2Cl·H2O with 35% probability ellipsoids, showing the atomic numbe...
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Figure 1: Possible reaction pathways in conjugate additions of nucleophiles on extended Michael acceptors.
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Figure 2: Early reports of conjugate addition of copper-based reagents to extended Michael acceptors.
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Figure 3: First applications of copper catalyzed 1,6-ACA in total synthesis.
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Scheme 1: First example of enantioselective copper-catalyzed ACA on an extended Michael acceptor.
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Scheme 2: Meldrum’s acid derivatives as substrates in enantioselective ACA.
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Scheme 3: Reactivity of a cyclic dienone in Cu-catalyzed ACA of diethylzinc.
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Scheme 4: Efficiency of DiPPAM ligand in 1,6-ACA of dialkylzinc to cyclic dienones.
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Scheme 5: Sequential 1,6/1,4-ACA reactions involving linear aryldienones.
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Scheme 6: Unsymmetrical hydroxyalkyl NHC ligands in 1,6-ACA of cyclic dienones.
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Scheme 7: Performance of atropoisomeric diphosphines in 1,6-ACA of Et2Zn on cyclic dienones.
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Scheme 8: Selective 1,6-ACA of Grignard reagents to acyclic dienoates, application in total synthesis.
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Scheme 9: Reactivity of polyenic linear thioesters towards sequential 1,6-ACA/reconjugation/1,4-ACA and produ...
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Scheme 10: 1,6-Conjugate addition of trialkylaluminium with regards to cyclic dienones.
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Scheme 11: Copper-catalyzed conjugate addition of trimethylaluminium onto nitro dienoates.
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Scheme 12: Copper-catalyzed selective 1,4-ACA in total synthesis of erogorgiaene.
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Scheme 13: 1,4-selective addition of diethylzinc onto a cyclic enynone catalyzed by a chiral NHC-based system.
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Scheme 14: Cu-NHC-catalyzed 1,6-ACA of dimethylzinc onto an α,β,γ,δ-unsaturated acyl-N-methylimidazole.
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Scheme 15: 1,4-Selectivity in conjugate addition on extended systems with the concomitant use of a chelating c...
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Scheme 16: Cu-NHC catalyzed 1,4-ACA as the key step in the total synthesis of ent-riccardiphenol B.
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Scheme 17: Cu-NHC-catalyzed 1,4-selective ACA reactions with enynones.
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Scheme 18: Linear dienones as substrates in 1,4-asymmetric conjugate addition reactions of Grignard reagents c...
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Scheme 19: 1,4-ACA of trimethylaluminium to a cyclic enynone catalyzed by a copper-NHC system.
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Scheme 20: Generation of a sterically encumbered chiral cyclohexanone from a polyunsaturated cyclic Michael ac...
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Scheme 21: Selective conversion of β,γ-unsaturated α-ketoesters in copper-catalyzed asymmetric conjugate addit...
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Scheme 22: Addition of trialkylaluminium compounds to nitroenynes catalyzed by L9/CuTC.
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Scheme 23: Addition of trialkylaluminium compounds to nitrodienes catalyzed by L9/CuTC.
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Scheme 24: Copper catalyzed 1,8- and 1,10-ACA reactions.
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Copper-catalysed asymmetric allylic alkylation of alkylzirconocenes to racemic 3,6-dihydro-2H-pyrans
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Scheme 1: Previously reported Cu-AAA of alkylzirconium reagents to racemic allyl chlorides [26] and this work.
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Figure 1: DoE from 3,6-dihydro-2H-pyran-3-yl diethyl phosphate (2d). Conditions: 4-phenyl-1-butene (2.5 equiv...
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Scheme 2: Scope of nucleophiles. Conditions: alkene (2.5 equiv), Cp2ZrHCl (2.0 equiv), 3-chloro-3,6-dihydro-2H...
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Figure 2: Reaction kinetics as monitored by in situ 1H NMR spectroscopy from 3-chloro-3,6-dihydro-2H-pyran (2a...
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Figure 3: Reaction kinetics as monitored by in situ 1H NMR spectroscopy from 3,6-dihydro-2H-pyran-3-yl diethy...
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Figure 4: Kinetic ee analysis using 2a. ee of reaction with 3-chloro-3,6-dihydro-2H-pyran (2a) as measured by...
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Figure 5: Kinetic ee analysis using 2d. ee of reaction with 3,6-dihydro-2H-pyran-3-yl diethyl phosphate (2d) ...
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- Published 04 Dec 2015
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Scheme 1: Conjugate addition of alkylborane 2a to alkynoate 3a.
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Scheme 2: Synthesis of five membered carbocycle.
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Scheme 3: Deuterium-labeling experiment.
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Figure 1: Possible mechanism.
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Figure 2: Isomerization of the alkenylcopper intermediates.
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Supp. Info
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- Published 11 Dec 2015
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Scheme 1: The synthesis of triazoles through the Huisgen cycloaddition of azides to alkynes.
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Scheme 2: The synthesis of symmetrically substituted 4,4'-bitriazoles.
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Scheme 3: The synthesis of unsymmetrically substituted 4,4'-bitriazoles.
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Scheme 4: The stepwise preparation of unsymmetrical 4,4'-bitriazoles.
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Scheme 5: The synthesis of 5,5'-bitriazoles.
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Scheme 6: The synthesis of bistriazoles and cyclic 5,5’-bitriazoles under different catalytic systems.
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Scheme 7: The double CuAAC reaction between helicenequinone and 1,1’-diazidoferrocene.
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Scheme 8: The synthesis of 1,2,3-triazoles and 5,5’-bitriazoles from acetylenic amide.
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Scheme 9: The amine-functionalized polysiloxane-mediated divergent synthesis of trizaoles and bitriazoles.
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Scheme 10: The cyclic BINOL-based 5,5’-bitriazoles.
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Scheme 11: The one-pot click–click reactions for the synthesis of bistriazoles.
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Scheme 12: The synthesis of bis(indolyl)methane-derivatized 1,2,3-bistriazoles.
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Scheme 13: The sequential, chemoselective preparation of bistriazoles.
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Scheme 14: The sequential SPAAC and CuAAC reaction for the preparation of bistriazoles.
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Scheme 15: The synthesis of D-mannitol-based bistriazoles.
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Scheme 16: The synthesis of ester-linked and amide-linked bistriazoles.
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Scheme 17: The synthesis of acenothiadiazole-based bistriazoles.
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Scheme 18: The pyrene-appended thiacalix[4]arene-based bistriazole.
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Scheme 19: The synthesis of triazole-based tetradentate ligands.
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Scheme 20: The synthesis of phenanthroline-2,9-bistriazoles.
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Scheme 21: The three-component reaction for the synthesis of bistriazoles.
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Scheme 22: The one-pot synthesis of bistriazoles.
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Scheme 23: The synthesis of polymer-bearing 1,2,3-bistriazole.
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Scheme 24: The synthesis of bistriazoles via a sequential one-pot reaction.
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- Review
- Published 15 Dec 2015
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Scheme 1: Copper-catalyzed asymmetric preparation of biaryl diacids by Ullmann coupling.
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Scheme 2: Intramolecular biaryl coupling of bis(iodotrimethoxybenzoyl)hexopyranose derivatives.
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Scheme 3: Preparation of 3,3’-disubstituted MeO-BIPHEP derivatives.
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Scheme 4: Enantioselective synthesis of trans-4,5,9,10-tetrahydroxy-9,10-dihydrophenanthrene.
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Scheme 5: Copper-catalyzed coupling of oxazoline-substituted aromatics to afford biaryl products with high di...
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Scheme 6: Total synthesis of O-permethyl-tellimagrandin I.
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Scheme 7: Total synthesis of (+)-gossypol.
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Scheme 8: Total synthesis of (−)-mastigophorene A.
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Scheme 9: Total synthesis of isokotanin.
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Scheme 10: Synthesis of dimethyl[7]thiaheterohelicenes.
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Scheme 11: Intramolecular coupling with chiral ortho-substituents.
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Scheme 12: Chiral 1,3-diol-derived tethers in the diastereoselective synthesis of biaryl compounds.
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Scheme 13: Synthesis of chiral unsymmetrically substituted biaryl compounds.
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Scheme 14: Atroposelective synthesis of biaryl ligands and natural products by using a chiral diether linker.
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Scheme 15: Enantioselective arylation reactions of 2-methylacetoacetates.
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Scheme 16: Asymmetric aryl C–N coupling reactions following a desymmetrization strategy.
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Scheme 17: Construction of cyano-bearing all-carbon quaternary stereocenters.
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Scheme 18: An unexpected inversion of the enantioselectivity in the asymmetric C–N coupling reactions using ch...
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Scheme 19: Differentiation of two nucleophilic amide groups.
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Scheme 20: Synthesis of spirobilactams through a double N-arylation reaction.
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Scheme 21: Asymmetric N-arylation through kinetic resolution.
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Scheme 22: Formation of cyano-substituted quaternary stereocenters through kinetic resolution.
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Scheme 23: Copper-catalyzed intramolecular desymmetric aryl C–O coupling.
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Scheme 24: Transition metal-catalyzed allylic substitutions.
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Scheme 25: Copper-catalyzed asymmetric allylic substitution of allyl phosphates.
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Scheme 26: Allylic substitution of allyl phosphates with allenylboronates.
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Scheme 27: Allylic substitution of allyl phosphates with vinylboron.
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Scheme 28: Allylic substitution of allyl phosphates with vinylboron.
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Scheme 29: Construction of quaternary stereogenic carbon centers through enantioselective allylic cross-coupli...
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Scheme 30: Cu-catalyzed enantioselective allyl–allyl cross-coupling.
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Scheme 31: Cu-catalyzed enantioselective allylic substitutions with silylboronates.
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Scheme 32: Asymmetric allylic substitution of allyl phosphates with silylboronates.
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Scheme 33: Stereoconvergent synthesis of chiral allylboronates.
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Scheme 34: Enantioselective allylic substitutions with diboronates.
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Scheme 35: Enantioselective allylic alkylations of terminal alkynes.
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- Review
- Published 18 Dec 2015
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Scheme 1: Trifluoromethylation using trifluoroacetate.
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Scheme 2: Decarboxylative pentafluoroethylation and its application.
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Scheme 3: Trifluoromethyation with trifluoroacetate in a flow system.
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Scheme 4: Trifluoromethylation of 4-bromotoluene by [(NHC)Cu(TFA)].
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Scheme 5: Trifluoromethylation of aryl iodides with small amounts of Cu and Ag2O. aThe yield was determined b...
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Scheme 6: C–H trifluoromethylation of arenes using trifluoroacetic acid.
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Scheme 7: CF3Cu generated from chlorofluoroacetate and CuI.
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Scheme 8: [18F]Trifluoromethyation with difluorocarbenes for PET. aRadiochemical yield determined by HPLC.
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Scheme 9: Trifluoromethylation with trifluoroacetate and copper iodide.
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Scheme 10: Preparation of trifluoromethylcopper from trifluoromethyl ketone.
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Scheme 11: Trifluoromethylation of aryl iodides. aIsolated yield. b1 equivalent each of CF3Cu reagent and 1,10...
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Scheme 12: Pentafluoroethylation of aryl bromides. aYield was determined by 19F NMR analysis using benzotriflu...
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Scheme 13: Perfluoroalkylation reactions of arylboronic acids. aIsolated yield. bDMF was used instead of tolue...
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Scheme 14: Trifluoromethylation with silylated hemiaminal of fluoral.
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Scheme 15: Catalytic trifluoromethylation with a fluoral derivative.
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Scheme 16: The scope of Cu-catalyzed aromatic trifluoromethylation. The yield was determined by 19F NMR analys...
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Scheme 17: Plausible mechanism of Cu-catalyzed aromatic trifluoromethylation [53].
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- Review
- Published 22 Dec 2015
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Figure 1: Chiral ligands utilized in copper-catalyzed alkynylations of cyclic iminium and oxocarbenium ions.
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Scheme 1: Li’s alkynylation of acyclic N-arylimines.
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Scheme 2: Knochel’s alkynylation of acyclic N-alkylenamines.
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Scheme 3: Li’s CDC of tetrahydroisoquinolines and alkynes.
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Scheme 4: Li’s alkynylation of N-aryldihydroisoquinolinium ions.
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Scheme 5: Schreiber’s alkynylation of N-alkylisoquinolinium ions.
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Scheme 6: Ma’s alkynylation of pyridium ions.
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Scheme 7: Arndtsen’s alkynylation of cyclic iminium ions.
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Scheme 8: Maruoka’s alkynylation of azomethine imines.
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Scheme 9: Su’s CDC of tetrahydroisoquinolines and alkynes under ball milling conditions.
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Scheme 10: Ma’s A3-coupling.
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Scheme 11: Li’s CDC reaction using photoredox catalysis.
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Scheme 12: Liu’s CDC reaction of N-carbamoyltetrahydroisoquinolines. T+BF4– = 2,2,6,6-tetramethylpiperidine N-...
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Scheme 13: Aponick’s alkynylation of N-carbomoylquinolinium ions using StackPhos as ligand.
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Scheme 14: Carreira’s enantioselective, catalytic alkynylation of aldehydes.
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Scheme 15: Watson’s alkynylation of isochroman oxocarbenium ions.
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Scheme 16: Watson’s alkynylation of chromene oxocarbenium ions.
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Scheme 17: Watson’s alkynylation to set diaryl tetrasubstituted stereocenters.
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- Letter
- Published 24 Dec 2015
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Figure 1: Bioactive compounds containing 1,2-aminoalcohol motif.
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Scheme 1: Copper-catalyzed radical aminooxygenation reaction of styrenes.
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Figure 2: The copper-catalyzed three-component aminooxygenation of styrenes with NFSI and NHPI derivatives. R...
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Scheme 2: The plausible mechanism.
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Scheme 3: Selective reduction of the aminooxygenation product.
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- Letter
- Published 07 Jan 2016
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Figure 1: Examples of valuable 1,2-oxyamino-containing molecules.
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Scheme 1: Strategies for intermolecular olefin oxyamination.
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Scheme 2: Examples of carboxylic acids in the olefin oxyamination reaction. Reaction conditions: 1 (1.2 mmol,...
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Scheme 3: Examples of O-benzoylhydroxylamines in the olefin oxyamination reaction. Reaction conditions: 1a (1...
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- Full Research Paper
- Published 11 Mar 2016
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Figure 1: Representative examples of triarylmethanes.
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Scheme 1: General methods and proposed method for the synthesis of triarylmethanes.
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Scheme 2: Role of solvent and reaction conditions in the Cu(OTf)2-mediated coupling of diphenylmethanol (9a) ...
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Scheme 3: A plausible mechanism for the formation of triarylmethanes 11.
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Scheme 4: Copper-catalyzed C–C bond formation synthesis of triarylmethane 10l.
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Scheme 5: Synthesis of anti-breast-cancer agent intermediate 22.
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- Published 22 Mar 2016
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Scheme 1: Selected examples of oligopeptides bearing dehydroamino acid moieties: myxovalargin (1), argyrin A (...
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Scheme 2: The Buchwald cross-coupling reaction in the preparation of peptides containing dehydroamino acids 4....
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Scheme 3: Syntheses of vinyl iodides 10 and 11.
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Scheme 4: Preparation of vinyl iodides 24–29 (Cbz = benzyloxycarbonyl, Alloc = allyloxycarbonyl, Boc = tert-b...
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Scheme 5: Copper-mediated C–N cross-coupling of dehydropeptides 31–33, 36, 37, and 39–41.
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Scheme 6: C–N coupling reaction between amide 43 and vinyl iodide 42; formation of dehydroisoleucine containi...
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