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Gold catalysis for organic synthesis


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.



 
Overview

Gold catalysis for organic synthesis

F. Dean Toste

Beilstein J. Org. Chem. 2011, 7, 553–554. published 04 May 2011

Editorial

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, Min Shi

Beilstein J. Org. Chem. 2011, 7, 555–564. published 04 May 2011

Full Research Paper

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

Jonathan P. Brand, Clara Chevalley, Jérôme Waser

Beilstein J. Org. Chem. 2011, 7, 565–569. published 04 May 2011

Letter

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

Sami F. Tlais, Gregory B. Dudley

Beilstein J. Org. Chem. 2011, 7, 570–577. published 04 May 2011

Full Research Paper

Construction of cyclic enones via gold-catalyzed oxygen transfer reactions

Leping Liu, Bo Xu, Gerald B. Hammond

Beilstein J. Org. Chem. 2011, 7, 606–614. published 13 May 2011

Review

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

Benito Alcaide, Pedro Almendros

Beilstein J. Org. Chem. 2011, 7, 622–630. published 17 May 2011

Review

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

Lei Zhou, Yizhou Liu, Yan Zhang, Jianbo Wang

Beilstein J. Org. Chem. 2011, 7, 631–637. published 18 May 2011

Full Research Paper

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

Haruo Aikawa, Tetsuro Kaneko, Naoki Asao, Yoshinori Yamamoto

Beilstein J. Org. Chem. 2011, 7, 648–652. published 20 May 2011

Letter

Gold-catalyzed naphthalene functionalization

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

Beilstein J. Org. Chem. 2011, 7, 653–657. published 23 May 2011

Full Research Paper

When cyclopropenes meet gold catalysts

Frédéric Miege, Christophe Meyer, Janine Cossy

Beilstein J. Org. Chem. 2011, 7, 717–734. published 30 May 2011

Review

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, Young Ho Rhee

Beilstein J. Org. Chem. 2011, 7, 740–743. published 01 Jun 2011

Letter

Synthetic applications of gold-catalyzed ring expansions

David Garayalde, Cristina Nevado

Beilstein J. Org. Chem. 2011, 7, 767–780. published 07 Jun 2011

Review

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

Dong Xing, Dan Yang

Beilstein J. Org. Chem. 2011, 7, 781–785. published 08 Jun 2011

Letter

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, Roberto Sanz

Beilstein J. Org. Chem. 2011, 7, 786–793. published 09 Jun 2011

Full Research Paper

High chemoselectivity in the phenol synthesis

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

Beilstein J. Org. Chem. 2011, 7, 794–801. published 10 Jun 2011

Full Research Paper

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

Berenger Biannic, Thomas Ghebreghiorgis, Aaron Aponick

Beilstein J. Org. Chem. 2011, 7, 802–807. published 14 Jun 2011

Full Research Paper

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

Deyun Qian, Junliang Zhang

Beilstein J. Org. Chem. 2011, 7, 808–812. published 15 Jun 2011

Full Research Paper

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

Paul W. Davies, Nicolas Martin, Neil Spencer

Beilstein J. Org. Chem. 2011, 7, 839–846. published 21 Jun 2011

Full Research Paper

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

Sara Hummel, Stefan F. Kirsch

Beilstein J. Org. Chem. 2011, 7, 847–859. published 22 Jun 2011

Review

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

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

Beilstein J. Org. Chem. 2011, 7, 860–865. published 24 Jun 2011

Full Research Paper

Gold-catalyzed propargylic substitutions: Scope and synthetic developments

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

Beilstein J. Org. Chem. 2011, 7, 866–877. published 28 Jun 2011

Review

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

Florin M. Istrate, Fabien Gagosz

Beilstein J. Org. Chem. 2011, 7, 878–885. published 29 Jun 2011

Letter

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

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

Beilstein J. Org. Chem. 2011, 7, 892–896. published 01 Jul 2011

Full Research Paper

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

He Huang, Yu Zhou, Hong Liu

Beilstein J. Org. Chem. 2011, 7, 897–936. published 04 Jul 2011

Review

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

Tetsuro Shibuya, Kyosuke Nakamura, Ken Tanaka

Beilstein J. Org. Chem. 2011, 7, 944–950. published 06 Jul 2011

Full Research Paper

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, Masaya Sawamura

Beilstein J. Org. Chem. 2011, 7, 951–959. published 08 Jul 2011

Full Research Paper

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, Fernando P. Cossío

Beilstein J. Org. Chem. 2011, 7, 988–996. published 19 Jul 2011

Full Research Paper

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, Louis Barriault

Beilstein J. Org. Chem. 2011, 7, 1007–1013. published 22 Jul 2011

Full Research Paper

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

Dawei Wang, Yanwei Zhang, Rong Cai, Xiaodong Shi

Beilstein J. Org. Chem. 2011, 7, 1014–1020. published 25 Jul 2011

Letter

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

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

Beilstein J. Org. Chem. 2011, 7, 1021–1029. published 26 Jul 2011

Full Research Paper

Recent developments in gold-catalyzed cycloaddition reactions

Fernando López, José L. Mascareñas

Beilstein J. Org. Chem. 2011, 7, 1075–1094. published 09 Aug 2011

Review

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, Chi-Ming Che

Beilstein J. Org. Chem. 2011, 7, 1100–1107. published 11 Aug 2011

Full Research Paper

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

Michel Chiarucci, Mirko Locritani, Gianpiero Cera, Marco Bandini

Beilstein J. Org. Chem. 2011, 7, 1198–1204. published 01 Sep 2011

Letter

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, Louis Fensterbank

Beilstein J. Org. Chem. 2011, 7, 1379–1386. published 07 Oct 2011

Full Research Paper

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

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

Beilstein J. Org. Chem. 2011, 7, 1520–1525. published 14 Nov 2011

Full Research Paper