. 2011:7:897-936.

doi: 10.3762/bjoc.7.103. Epub 2011 Jul 4.

Recent advances in the gold-catalyzed additions to C-C multiple bonds

He Huang¹, Yu Zhou, Hong Liu

Affiliations

PMID: 21804887
PMCID: PMC3135236
DOI: 10.3762/bjoc.7.103

Recent advances in the gold-catalyzed additions to C-C multiple bonds

He Huang et al. Beilstein J Org Chem. 2011.

. 2011:7:897-936.

doi: 10.3762/bjoc.7.103. Epub 2011 Jul 4.

Authors

He Huang¹, Yu Zhou, Hong Liu

Affiliation

¹ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.

PMID: 21804887
PMCID: PMC3135236
DOI: 10.3762/bjoc.7.103

Abstract

C-O, C-N and C-C bonds are the most widespread types of bonds in nature, and are the cornerstone of most organic compounds, ranging from pharmaceuticals and agrochemicals to advanced materials and polymers. Cationic gold acts as a soft and carbophilic Lewis acid and is considered one of the most powerful activators of C-C multiple bonds. Consequently, gold-catalysis plays an important role in the development of new strategies to form these bonds in more convenient ways. In this review, we highlight recent advances in the gold-catalyzed chemistry of addition of X-H (X = O, N, C) bonds to C-C multiple bonds, tandem reactions, and asymmetric additions. This review covers gold-catalyzed organic reactions published from 2008 to the present.

Keywords: C−C multiple bonds; asymmetric addition; catalysis; gold; tandem reaction.

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Figures

**Scheme 1**
Gold-catalyzed addition of alcohols.

**Scheme 2**
Gold-catalyzed cycloaddition of alcohols.

**Scheme 3**
Ionic liquids as the solvent in gold-catalyzed cycloaddition.

**Scheme 4**
Gold-catalyzed cycloaddition of diynes.

**Scheme 5**
Gold(I) chloride catalyzed cycloisomerization of 2-alkynyl-1,5-diols.

**Scheme 6**
Gold-catalyzed cycloaddition of glycols and dihydroxy compounds.

**Scheme 7**
Gold-catalyzed ring-opening of cyclopropenes.

**Scheme 8**
Gold-catalyzed intermolecular hydroalkoxylation of alkynes. PR₃ = **41–45**.

**Scheme 9**
Gold-catalyzed intramolecular 6-endo-dig cyclization of β-hydroxy-α,α-difluoroynones.

**Scheme 10**
Gold-catalyzed intermolecular hydroalkoxylation of non-activated olefins.

**Scheme 11**
Preparation of unsymmetrical ethers from alcohols.

**Scheme 12**
Expedient synthesis of dihydrofuran-3-ones.

**Scheme 13**
Catalytic approach to functionalized divinyl ketones.

**Scheme 14**
Gold-catalyzed glycosylation.

**Scheme 15**
Gold-catalyzed cycloaddition of aldehydes and ketones.

**Scheme 16**
Gold-catalyzed annulations of 2-(ynol)aryl aldehydes and o-alkynyl benzaldehydes.

**Scheme 17**
Gold-catalyzed addition of carboxylates.

**Scheme 18**
Dual-catalyzed rearrangement reaction of allenoates.

**Scheme 19**
Meyer–Schuster rearrangement of propargylic alcohols.

**Scheme 20**
Propargylic alcohol rearrangements.

**Scheme 21**
Gold-catalyzed synthesis of imines and amine alkylation.

**Scheme 22**
Hydroamination of allenes and allenamides.

**Scheme 23**
Gold-catalyzed inter- and intramolecular amination of alkynes and alkenes.

**Scheme 24**
Gold-catalyzed cycloisomerization of O-propioloyl oximes and β-allenylhydrazones.

**Scheme 25**
Intra- and intermolecular amination with ureas.

**Scheme 26**
Gold-catalyzed cyclization of *ortho*-alkynyl-N-sulfonylanilines and but-3-yn-1-amines.

**Scheme 27**
Gold-catalyzed piperidine ring synthesis.

**Scheme 28**
Ring expansion of alkylnyl cyclopropanes.

**Scheme 29**
Gold-catalyzed annulations of N-propargyl-β-enaminones and azomethine imines.

**Scheme 30**
Gold(I)-catalyzed cycloisomerization of aziridines.

**Scheme 31**
AuCl₃/AgSbF₆-catalyzed intramolecular amination of 2-(tosylamino)phenylprop-1-en-3-ols.

**Scheme 32**
Gold-catalyzed cyclization via a 7-endo-dig pathway.

**Scheme 33**
Gold-catalyzed synthesis of fused xanthines.

**Scheme 34**
Gold-catalyzed synthesis of amides and isoquinolines.

**Scheme 35**
Gold-catalyzed oxidative cross-coupling reactions of propargylic acetates.

**Scheme 36**
Gold-catalyzed nucleophilic addition to allenamides.

**Scheme 37**
Gold-catalyzed direct carbon–carbon bond coupling reactions.

**Scheme 38**
Gold-catalyzed C−H functionalization of indole/pyrrole heterocycles and non-activated arenes.

**Scheme 39**
Gold-catalyzed cycloisomerization of cyclic compounds.

**Scheme 40**
Gold-catalyzed cycloaddition of 1-aryl-1-allen-6-enes and propargyl acetates.

**Scheme 41**
Gold(I)-catalyzed cycloaddition with ligand-controlled regiochemistry.

**Scheme 42**
Gold(I)-catalyzed cycloaddition of dienes and enynes.

**Scheme 43**
Gold-catalyzed intramolecular cycloaddition of 3-alkoxy-1,5-enynes and 2,2-dipropargylmalonates.

**Scheme 44**
Gold-catalyzed intramolecular cycloaddition of 1,5-allenynes.

**Scheme 45**
Gold(I)-catalyzed cycloaddition of indoles.

**Scheme 46**
Gold-catalyzed annulation reactions.

**Scheme 47**
Gold–carbenoid induced cleavage of a sp³-hybridized C−H bond.

**Scheme 48**
Furan- and indole-based cascade reactions.

**Scheme 49**
Tandem process using aromatic alkynes.

**Scheme 50**
Gold-catalyzed cycloaddition of 1,3-dien-5-ynes.

**Scheme 51**
Gold-catalyzed cascade cyclization of diynes, propargylic esters, and 1,3-enynyl ketones.

**Scheme 52**
Tandem reaction of β-phenoxyimino ketones and alkynyl oxime ethers.

**Scheme 53**
Gold-catalyzed tandem cyclization of enynes, 2-(tosylamino)phenylprop-1-yn-3-ols, and allenoates.

**Scheme 54**
Cyclization of 2,4-dien-6-yne carboxylic acids.

**Scheme 55**
Gold(I)-catalyzed tandem cyclization approach to tetracyclic indolines.

**Scheme 56**
Gold-catalyzed tandem reactions of alkynes.

**Scheme 57**
Aminoarylation and oxyarylation of alkenes.

**Scheme 58**
Cycloaddition of 2-ethynylnitrobenzene with various alkenes.

**Scheme 59**
Gold-catalyzed tandem reactions of allenoates and alkynes.

**Scheme 60**
Gold-catalyzed asymmetric synthesis of 2,3-dihydropyrroles.

**Scheme 61**
Chiral [NHC–Au(I)]-catalyzed cyclization of enyne.

**Scheme 62**
Gold-catalyzed hydroaminations and hydroalkoxylations.

**Scheme 63**
Gold(I)-catalyzed asymmetric hydroalkoxylation of 1,3-dihydroxymethyl-2-alkynylbenzene chromium complexes.

**Scheme 64**
Gold-catalyzed synthesis of julolidine derivatives.

**Scheme 65**
Gold-catalyzed the synthesis of chiral fused heterocycles.

**Scheme 66**
Gold-catalyzed asymmetric reactions with 3,5-(t-Bu)₂-4-MeO-MeOBIPHEP.

**Scheme 67**
Gold-catalyzed cyclization of o-(alkynyl) styrenes.

**Scheme 68**
Asymmetric gold(I)-catalyzed redox-neutral domino reactions of enynes.

**Scheme 69**
Gold(I)-catalyzed enantioselective polyene cyclization reaction.

**Scheme 70**
Gold(I)-catalyzed enantioselective synthesis of benzopyrans.

**Scheme 71**
Gold(I)-catalyzed enantioselective ring expansion of allenylcyclopropanols.

See this image and copyright information in PMC

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Recent advances in the gold-catalyzed additions to C-C multiple bonds

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Recent advances in the gold-catalyzed additions to C-C multiple bonds

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