Gold catalysis for organic synthesis

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Editor: F. Dean Toste
University of California, Berkeley
 
The past decade has witnessed a remarkable growth in the number of organic reactions that are catalyzed by homogeneous gold complexes. Many of the early reported reactions took advantage of the propensity of gold complexes to serve as excellent catalysts for reactions that proceed through π-activation of carbon–carbon multiple bonds. Subsequently, the reactivity paradigms available for gold complexes have proven to be almost limitless. The contributions from many research groups underscore the growing importance of homogenous gold catalysis. More importantly, the papers in this Thematic Series highlight the remarkable breath of reactivity that can be accessed using homogenous gold complexes as catalysts; from catalysis of sigmatropic rearrangement, cycloaddition and cycloisomerization reactions, to applications in enantioselective catalysis, oxidative coupling and the total synthesis of natural products, and transformations of alkynes, allenes, alkenes and even C–H bonds.

See also the Thematic Series:
Gold catalysis for organic synthesis II
Copper catalysis in organic synthesis
Transition-metal and organocatalysis in natural product synthesis

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Gold catalysis for organic synthesis

  • F. Dean Toste

Beilstein J. Org. Chem. 2011, 7, 553–554, doi:10.3762/bjoc.7.63

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Published 04 May 2011

Synthesis of chiral mono(N-heterocyclic carbene) palladium and gold complexes with a 1,1'-biphenyl scaffold and their applications in catalysis

  • Lian-jun Liu,
  • Feijun Wang,
  • Wenfeng Wang,
  • Mei-xin Zhao and
  • Min Shi

Beilstein J. Org. Chem. 2011, 7, 555–564, doi:10.3762/bjoc.7.64

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Published 04 May 2011

One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines

  • Jonathan P. Brand,
  • Clara Chevalley and
  • Jérôme Waser

Beilstein J. Org. Chem. 2011, 7, 565–569, doi:10.3762/bjoc.7.65

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Published 04 May 2011

A gold-catalyzed alkyne-diol cycloisomerization for the synthesis of oxygenated 5,5-spiroketals

  • Sami F. Tlais and
  • Gregory B. Dudley

Beilstein J. Org. Chem. 2011, 7, 570–577, doi:10.3762/bjoc.7.66

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Published 04 May 2011

Construction of cyclic enones via gold-catalyzed oxygen transfer reactions

  • Leping Liu,
  • Bo Xu and
  • Gerald B. Hammond

Beilstein J. Org. Chem. 2011, 7, 606–614, doi:10.3762/bjoc.7.71

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Published 13 May 2011

Gold-catalyzed heterocyclizations in alkynyl- and allenyl-β-lactams

  • Benito Alcaide and
  • Pedro Almendros

Beilstein J. Org. Chem. 2011, 7, 622–630, doi:10.3762/bjoc.7.73

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Published 17 May 2011

Sequential Au(I)-catalyzed reaction of water with o-acetylenyl-substituted phenyldiazoacetates

  • Lei Zhou,
  • Yizhou Liu,
  • Yan Zhang and
  • Jianbo Wang

Beilstein J. Org. Chem. 2011, 7, 631–637, doi:10.3762/bjoc.7.74

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Published 18 May 2011

Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters

  • Haruo Aikawa,
  • Tetsuro Kaneko,
  • Naoki Asao and
  • Yoshinori Yamamoto

Beilstein J. Org. Chem. 2011, 7, 648–652, doi:10.3762/bjoc.7.76

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Published 20 May 2011

Gold-catalyzed naphthalene functionalization

  • Pedro J. Pérez,
  • M. Mar Díaz-Requejo and
  • Iván Rivilla

Beilstein J. Org. Chem. 2011, 7, 653–657, doi:10.3762/bjoc.7.77

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Published 23 May 2011

When cyclopropenes meet gold catalysts

  • Frédéric Miege,
  • Christophe Meyer and
  • Janine Cossy

Beilstein J. Org. Chem. 2011, 7, 717–734, doi:10.3762/bjoc.7.82

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Published 30 May 2011

A racemic formal total synthesis of clavukerin A using gold(I)-catalyzed cycloisomerization of 3-methoxy-1,6-enynes as the key strategy

  • Jae Youp Cheong and
  • Young Ho Rhee

Beilstein J. Org. Chem. 2011, 7, 740–743, doi:10.3762/bjoc.7.84

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Published 01 Jun 2011

Synthetic applications of gold-catalyzed ring expansions

  • David Garayalde and
  • Cristina Nevado

Beilstein J. Org. Chem. 2011, 7, 767–780, doi:10.3762/bjoc.7.87

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Published 07 Jun 2011

Highly efficient gold(I)-catalyzed Overman rearrangement in water

  • Dong Xing and
  • Dan Yang

Beilstein J. Org. Chem. 2011, 7, 781–785, doi:10.3762/bjoc.7.88

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Published 08 Jun 2011

Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindoles

  • Estela Álvarez,
  • Delia Miguel,
  • Patricia García-García,
  • Manuel A. Fernández-Rodríguez,
  • Félix Rodríguez and
  • Roberto Sanz

Beilstein J. Org. Chem. 2011, 7, 786–793, doi:10.3762/bjoc.7.89

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Published 09 Jun 2011

High chemoselectivity in the phenol synthesis

  • Matthias Rudolph,
  • Melissa Q. McCreery,
  • Wolfgang Frey and
  • A. Stephen K. Hashmi

Beilstein J. Org. Chem. 2011, 7, 794–801, doi:10.3762/bjoc.7.90

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Published 10 Jun 2011

A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers

  • Berenger Biannic,
  • Thomas Ghebreghiorgis and
  • Aaron Aponick

Beilstein J. Org. Chem. 2011, 7, 802–807, doi:10.3762/bjoc.7.91

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Published 14 Jun 2011

Au(I)/Au(III)-catalyzed Sonogashira-type reactions of functionalized terminal alkynes with arylboronic acids under mild conditions

  • Deyun Qian and
  • Junliang Zhang

Beilstein J. Org. Chem. 2011, 7, 808–812, doi:10.3762/bjoc.7.92

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Published 15 Jun 2011

Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines

  • Paul W. Davies,
  • Nicolas Martin and
  • Neil Spencer

Beilstein J. Org. Chem. 2011, 7, 839–846, doi:10.3762/bjoc.7.96

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Published 21 Jun 2011

When gold can do what iodine cannot do: A critical comparison

  • Sara Hummel and
  • Stefan F. Kirsch

Beilstein J. Org. Chem. 2011, 7, 847–859, doi:10.3762/bjoc.7.97

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Published 22 Jun 2011

Gold-catalyzed oxidation of arylallenes: Synthesis of quinoxalines and benzimidazoles

  • Dong-Mei Cui,
  • Dan-Wen Zhuang,
  • Ying Chen and
  • Chen Zhang

Beilstein J. Org. Chem. 2011, 7, 860–865, doi:10.3762/bjoc.7.98

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Published 24 Jun 2011

Gold-catalyzed propargylic substitutions: Scope and synthetic developments

  • Olivier Debleds,
  • Eric Gayon,
  • Emmanuel Vrancken and
  • Jean-Marc Campagne

Beilstein J. Org. Chem. 2011, 7, 866–877, doi:10.3762/bjoc.7.99

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Published 28 Jun 2011

Gold(I)-catalyzed formation of furans by a Claisen-type rearrangement of ynenyl allyl ethers

  • Florin M. Istrate and
  • Fabien Gagosz

Beilstein J. Org. Chem. 2011, 7, 878–885, doi:10.3762/bjoc.7.100

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Published 29 Jun 2011

The role of silver additives in gold-mediated C–H functionalisation

  • Scott R. Patrick,
  • Ine I. F. Boogaerts,
  • Sylvain Gaillard,
  • Alexandra M. Z. Slawin and
  • Steven P. Nolan

Beilstein J. Org. Chem. 2011, 7, 892–896, doi:10.3762/bjoc.7.102

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Published 01 Jul 2011

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

  • He Huang,
  • Yu Zhou and
  • Hong Liu

Beilstein J. Org. Chem. 2011, 7, 897–936, doi:10.3762/bjoc.7.103

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Published 04 Jul 2011

Cationic gold(I) axially chiral biaryl bisphosphine complex-catalyzed atropselective synthesis of heterobiaryls

  • Tetsuro Shibuya,
  • Kyosuke Nakamura and
  • Ken Tanaka

Beilstein J. Org. Chem. 2011, 7, 944–950, doi:10.3762/bjoc.7.105

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Published 06 Jul 2011

Intramolecular hydroamination of alkynic sulfonamides catalyzed by a gold–triethynylphosphine complex: Construction of azepine frameworks by 7-exo-dig cyclization

  • Hideto Ito,
  • Tomoya Harada,
  • Hirohisa Ohmiya and
  • Masaya Sawamura

Beilstein J. Org. Chem. 2011, 7, 951–959, doi:10.3762/bjoc.7.106

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Published 08 Jul 2011

Chiral gold(I) vs chiral silver complexes as catalysts for the enantioselective synthesis of the second generation GSK-hepatitis C virus inhibitor

  • María Martín-Rodríguez,
  • Carmen Nájera,
  • José M. Sansano,
  • Abel de Cózar and
  • Fernando P. Cossío

Beilstein J. Org. Chem. 2011, 7, 988–996, doi:10.3762/bjoc.7.111

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Published 19 Jul 2011

One-pot Diels–Alder cycloaddition/gold(I)-catalyzed 6-endo-dig cyclization for the synthesis of the complex bicyclo[3.3.1]alkenone framework

  • Boubacar Sow,
  • Gabriel Bellavance,
  • Francis Barabé and
  • Louis Barriault

Beilstein J. Org. Chem. 2011, 7, 1007–1013, doi:10.3762/bjoc.7.114

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Published 22 Jul 2011

Triazole–Au(I) complex as chemoselective catalyst in promoting propargyl ester rearrangements

  • Dawei Wang,
  • Yanwei Zhang,
  • Rong Cai and
  • Xiaodong Shi

Beilstein J. Org. Chem. 2011, 7, 1014–1020, doi:10.3762/bjoc.7.115

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Published 25 Jul 2011

Asymmetric Au-catalyzed cycloisomerization of 1,6-enynes: An entry to bicyclo[4.1.0]heptene

  • Alexandre Pradal,
  • Chung-Meng Chao,
  • Patrick Y. Toullec and
  • Véronique Michelet

Beilstein J. Org. Chem. 2011, 7, 1021–1029, doi:10.3762/bjoc.7.116

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Published 26 Jul 2011

Recent developments in gold-catalyzed cycloaddition reactions

  • Fernando López and
  • José L. Mascareñas

Beilstein J. Org. Chem. 2011, 7, 1075–1094, doi:10.3762/bjoc.7.124

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Published 09 Aug 2011

Efficient gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation of unactivated alkenes with α-ketones

  • Ya-Ping Xiao,
  • Xin-Yuan Liu and
  • Chi-Ming Che

Beilstein J. Org. Chem. 2011, 7, 1100–1107, doi:10.3762/bjoc.7.126

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Published 11 Aug 2011

Gold(I)-catalyzed synthesis of γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with alcohols

  • Michel Chiarucci,
  • Mirko Locritani,
  • Gianpiero Cera and
  • Marco Bandini

Beilstein J. Org. Chem. 2011, 7, 1198–1204, doi:10.3762/bjoc.7.139

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Published 01 Sep 2011

Combination of gold catalysis and Selectfluor for the synthesis of fluorinated nitrogen heterocycles

  • Antoine Simonneau,
  • Pierre Garcia,
  • Jean-Philippe Goddard,
  • Virginie Mouriès-Mansuy,
  • Max Malacria and
  • Louis Fensterbank

Beilstein J. Org. Chem. 2011, 7, 1379–1386, doi:10.3762/bjoc.7.162

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Published 07 Oct 2011

Synthesis of fluoranthenes by hydroarylation of alkynes catalyzed by gold(I) or gallium trichloride

  • Sergio Pascual,
  • Christophe Bour,
  • Paula de Mendoza and
  • Antonio M. Echavarren

Beilstein J. Org. Chem. 2011, 7, 1520–1525, doi:10.3762/bjoc.7.178

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Published 14 Nov 2011
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