4.8 Article

Arylsilanes: Application to Gold-Catalyzed Oxyarylation of Alkenes

Journal

ORGANIC LETTERS
Volume 12, Issue 21, Pages 4724-4727

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol1019162

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Funding

  1. EPSRC [EP/G036764/1]
  2. AstraZeneca
  3. GlaxoSmithKline
  4. Novartis
  5. Pfizer
  6. Syngenta
  7. University of Bristol
  8. Royal Society

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Arylsilanes are efficient reagents for the gold-catalyzed oxyarylation of alkenes (21 examples, up to 85% isolated yield). Using commercially available Ph3PAuCl 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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