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Arylsilanes: Application to Gold-Catalyzed Oxyarylation of Alkenes

Liam T. Ball, Michael Green, Guy C. Lloyd-Jones* and Christopher A. Russell*

*School of Chemistry, University of Bristol, Cantock’s Close, Bristol, United Kingdom BS8 1TS, Email: guy.lloyd-jonesbristol.ac.uk, chris.russellbristol.ac.uk

L. T. Ball, M. Green G. C. Lloyd-Jones, C. A. Russel, Org. Lett., 2010, 12, 4724-4727.

DOI: 10.1021/ol1019162 (free Supporting Information)


Abstract

Using commercially available Ph3PAuCl and readily prepared, benign arylsilanes, a gold-catalyzed oxyarylation of alkenes proceeds 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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Key Words

Arylation, Hydroxylation, Etherification, Selectfluor, Multicomponent Reactions


ID: J54-Y2010-2980