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. 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 Huang  1 , Yu Zhou, Hong Liu
Affiliations

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

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

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
Scheme 1
Gold-catalyzed addition of alcohols.
Scheme 2
Scheme 2
Gold-catalyzed cycloaddition of alcohols.
Scheme 3
Scheme 3
Ionic liquids as the solvent in gold-catalyzed cycloaddition.
Scheme 4
Scheme 4
Gold-catalyzed cycloaddition of diynes.
Scheme 5
Scheme 5
Gold(I) chloride catalyzed cycloisomerization of 2-alkynyl-1,5-diols.
Scheme 6
Scheme 6
Gold-catalyzed cycloaddition of glycols and dihydroxy compounds.
Scheme 7
Scheme 7
Gold-catalyzed ring-opening of cyclopropenes.
Scheme 8
Scheme 8
Gold-catalyzed intermolecular hydroalkoxylation of alkynes. PR3 = 41–45.
Scheme 9
Scheme 9
Gold-catalyzed intramolecular 6-endo-dig cyclization of β-hydroxy-α,α-difluoroynones.
Scheme 10
Scheme 10
Gold-catalyzed intermolecular hydroalkoxylation of non-activated olefins.
Scheme 11
Scheme 11
Preparation of unsymmetrical ethers from alcohols.
Scheme 12
Scheme 12
Expedient synthesis of dihydrofuran-3-ones.
Scheme 13
Scheme 13
Catalytic approach to functionalized divinyl ketones.
Scheme 14
Scheme 14
Gold-catalyzed glycosylation.
Scheme 15
Scheme 15
Gold-catalyzed cycloaddition of aldehydes and ketones.
Scheme 16
Scheme 16
Gold-catalyzed annulations of 2-(ynol)aryl aldehydes and o-alkynyl benzaldehydes.
Scheme 17
Scheme 17
Gold-catalyzed addition of carboxylates.
Scheme 18
Scheme 18
Dual-catalyzed rearrangement reaction of allenoates.
Scheme 19
Scheme 19
Meyer–Schuster rearrangement of propargylic alcohols.
Scheme 20
Scheme 20
Propargylic alcohol rearrangements.
Scheme 21
Scheme 21
Gold-catalyzed synthesis of imines and amine alkylation.
Scheme 22
Scheme 22
Hydroamination of allenes and allenamides.
Scheme 23
Scheme 23
Gold-catalyzed inter- and intramolecular amination of alkynes and alkenes.
Scheme 24
Scheme 24
Gold-catalyzed cycloisomerization of O-propioloyl oximes and β-allenylhydrazones.
Scheme 25
Scheme 25
Intra- and intermolecular amination with ureas.
Scheme 26
Scheme 26
Gold-catalyzed cyclization of ortho-alkynyl-N-sulfonylanilines and but-3-yn-1-amines.
Scheme 27
Scheme 27
Gold-catalyzed piperidine ring synthesis.
Scheme 28
Scheme 28
Ring expansion of alkylnyl cyclopropanes.
Scheme 29
Scheme 29
Gold-catalyzed annulations of N-propargyl-β-enaminones and azomethine imines.
Scheme 30
Scheme 30
Gold(I)-catalyzed cycloisomerization of aziridines.
Scheme 31
Scheme 31
AuCl3/AgSbF6-catalyzed intramolecular amination of 2-(tosylamino)phenylprop-1-en-3-ols.
Scheme 32
Scheme 32
Gold-catalyzed cyclization via a 7-endo-dig pathway.
Scheme 33
Scheme 33
Gold-catalyzed synthesis of fused xanthines.
Scheme 34
Scheme 34
Gold-catalyzed synthesis of amides and isoquinolines.
Scheme 35
Scheme 35
Gold-catalyzed oxidative cross-coupling reactions of propargylic acetates.
Scheme 36
Scheme 36
Gold-catalyzed nucleophilic addition to allenamides.
Scheme 37
Scheme 37
Gold-catalyzed direct carbon–carbon bond coupling reactions.
Scheme 38
Scheme 38
Gold-catalyzed C−H functionalization of indole/pyrrole heterocycles and non-activated arenes.
Scheme 39
Scheme 39
Gold-catalyzed cycloisomerization of cyclic compounds.
Scheme 40
Scheme 40
Gold-catalyzed cycloaddition of 1-aryl-1-allen-6-enes and propargyl acetates.
Scheme 41
Scheme 41
Gold(I)-catalyzed cycloaddition with ligand-controlled regiochemistry.
Scheme 42
Scheme 42
Gold(I)-catalyzed cycloaddition of dienes and enynes.
Scheme 43
Scheme 43
Gold-catalyzed intramolecular cycloaddition of 3-alkoxy-1,5-enynes and 2,2-dipropargylmalonates.
Scheme 44
Scheme 44
Gold-catalyzed intramolecular cycloaddition of 1,5-allenynes.
Scheme 45
Scheme 45
Gold(I)-catalyzed cycloaddition of indoles.
Scheme 46
Scheme 46
Gold-catalyzed annulation reactions.
Scheme 47
Scheme 47
Gold–carbenoid induced cleavage of a sp3-hybridized C−H bond.
Scheme 48
Scheme 48
Furan- and indole-based cascade reactions.
Scheme 49
Scheme 49
Tandem process using aromatic alkynes.
Scheme 50
Scheme 50
Gold-catalyzed cycloaddition of 1,3-dien-5-ynes.
Scheme 51
Scheme 51
Gold-catalyzed cascade cyclization of diynes, propargylic esters, and 1,3-enynyl ketones.
Scheme 52
Scheme 52
Tandem reaction of β-phenoxyimino ketones and alkynyl oxime ethers.
Scheme 53
Scheme 53
Gold-catalyzed tandem cyclization of enynes, 2-(tosylamino)phenylprop-1-yn-3-ols, and allenoates.
Scheme 54
Scheme 54
Cyclization of 2,4-dien-6-yne carboxylic acids.
Scheme 55
Scheme 55
Gold(I)-catalyzed tandem cyclization approach to tetracyclic indolines.
Scheme 56
Scheme 56
Gold-catalyzed tandem reactions of alkynes.
Scheme 57
Scheme 57
Aminoarylation and oxyarylation of alkenes.
Scheme 58
Scheme 58
Cycloaddition of 2-ethynylnitrobenzene with various alkenes.
Scheme 59
Scheme 59
Gold-catalyzed tandem reactions of allenoates and alkynes.
Scheme 60
Scheme 60
Gold-catalyzed asymmetric synthesis of 2,3-dihydropyrroles.
Scheme 61
Scheme 61
Chiral [NHC–Au(I)]-catalyzed cyclization of enyne.
Scheme 62
Scheme 62
Gold-catalyzed hydroaminations and hydroalkoxylations.
Scheme 63
Scheme 63
Gold(I)-catalyzed asymmetric hydroalkoxylation of 1,3-dihydroxymethyl-2-alkynylbenzene chromium complexes.
Scheme 64
Scheme 64
Gold-catalyzed synthesis of julolidine derivatives.
Scheme 65
Scheme 65
Gold-catalyzed the synthesis of chiral fused heterocycles.
Scheme 66
Scheme 66
Gold-catalyzed asymmetric reactions with 3,5-(t-Bu)2-4-MeO-MeOBIPHEP.
Scheme 67
Scheme 67
Gold-catalyzed cyclization of o-(alkynyl) styrenes.
Scheme 68
Scheme 68
Asymmetric gold(I)-catalyzed redox-neutral domino reactions of enynes.
Scheme 69
Scheme 69
Gold(I)-catalyzed enantioselective polyene cyclization reaction.
Scheme 70
Scheme 70
Gold(I)-catalyzed enantioselective synthesis of benzopyrans.
Scheme 71
Scheme 71
Gold(I)-catalyzed enantioselective ring expansion of allenylcyclopropanols.
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