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.
Gold catalysis for organic synthesisF. 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 catalysisLian-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-alkynylanilinesJonathan 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-spiroketalsSami 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 reactionsLeping 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-lactamsBenito 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 phenyldiazoacetatesLei 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 estersHaruo Aikawa, Tetsuro Kaneko, Naoki Asao, Yoshinori Yamamoto Beilstein J. Org. Chem. 2011, 7, 648–652. published 20 May 2011 Letter |
Gold-catalyzed naphthalene functionalizationPedro 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 catalystsFrédéric 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 strategyJae Youp Cheong, Young Ho Rhee Beilstein J. Org. Chem. 2011, 7, 740–743. published 01 Jun 2011 Letter |
Synthetic applications of gold-catalyzed ring expansionsDavid Garayalde, Cristina Nevado Beilstein J. Org. Chem. 2011, 7, 767–780. published 07 Jun 2011 Review |
Highly efficient gold(I)-catalyzed Overman rearrangement in waterDong 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-propargylindolesEstela 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 synthesisMatthias 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 ethersBerenger 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 conditionsDeyun 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 aziridinesPaul 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 comparisonSara 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 benzimidazolesDong-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 developmentsOlivier 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 ethersFlorin 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 functionalisationScott 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 bondsHe 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 heterobiarylsTetsuro 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 cyclizationHideto 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 inhibitorMaría 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 frameworkBoubacar 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 rearrangementsDawei 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]hepteneAlexandre 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 reactionsFernando 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-ketonesYa-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 alcoholsMichel 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 heterocyclesAntoine 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 trichlorideSergio Pascual, Christophe Bour, Paula de Mendoza, Antonio M. Echavarren Beilstein J. Org. Chem. 2011, 7, 1520–1525. published 14 Nov 2011 Full Research Paper |

