Literature DB >> 20879724

Arylsilanes: application to gold-catalyzed oxyarylation of alkenes.

Liam T Ball1, Michael Green, Guy C Lloyd-Jones, Christopher A Russell.   

Abstract

Arylsilanes are efficient reagents for the gold-catalyzed oxyarylation of alkenes (21 examples, up to 85% isolated yield). Using commercially available Ph(3)PAuCl and readily prepared, benign arylsilanes, these two- and three-component reactions proceed smoothly in air. The oxidant, Selectfluor, not only facilitates entry to the Au(I/III) manifold but also provides a fluoride anion for silane activation, thereby avoiding the need for addition of a stoichiometric base.

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Year:  2010        PMID: 20879724     DOI: 10.1021/ol1019162

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  24 in total

1.  Copper-catalyzed intramolecular alkene carboetherification: synthesis of fused-ring and bridged-ring tetrahydrofurans.

Authors:  Yan Miller; Lei Miao; Azade S Hosseini; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2012-07-05       Impact factor: 15.419

2.  Two metals are better than one in the gold catalyzed oxidative heteroarylation of alkenes.

Authors:  Ekaterina Tkatchouk; Neal P Mankad; Diego Benitez; William A Goddard; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-08-23       Impact factor: 15.419

3.  Gold-catalyzed allylation of aryl boronic acids: accessing cross-coupling reactivity with gold.

Authors:  Mark D Levin; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-05       Impact factor: 15.336

4.  Iron-catalyzed cross-coupling of unactivated secondary alkyl thio ethers and sulfones with aryl Grignard reagents.

Authors:  Scott E Denmark; Alexander J Cresswell
Journal:  J Org Chem       Date:  2013-11-20       Impact factor: 4.354

5.  Pd(0)/Au(I) redox incompatibilities as revealed by Pd-catalyzed homo-coupling of arylgold(I)-complexes.

Authors:  Dieter Weber; Michel R Gagné
Journal:  Chem Commun (Camb)       Date:  2011-03-31       Impact factor: 6.222

6.  Stable Au(I) catalysts for oxidant-free C-H Functionalization with Iodoarenes.

Authors:  R Tyler Mertens; Charles E Greif; James T Coogle; Gilles Berger; Sean Parkin; Mark D Watson; Samuel G Awuah
Journal:  J Catal       Date:  2022-02-28       Impact factor: 7.920

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

Authors:  He Huang; Yu Zhou; Hong Liu
Journal:  Beilstein J Org Chem       Date:  2011-07-04       Impact factor: 2.883

Review 8.  Homogeneous Gold-Catalyzed Oxidation Reactions.

Authors:  Zhitong Zheng; Xu Ma; Xinpeng Cheng; Ke Zhao; Kaylaa Gutman; Tianyou Li; Liming Zhang
Journal:  Chem Rev       Date:  2021-02-16       Impact factor: 72.087

9.  Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes.

Authors:  Rong Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2015-06-23       Impact factor: 15.419

10.  Dual visible light photoredox and gold-catalyzed arylative ring expansion.

Authors:  Xing-zhong Shu; Miao Zhang; Ying He; Heinz Frei; F Dean Toste
Journal:  J Am Chem Soc       Date:  2014-04-14       Impact factor: 15.419

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