Arylsilanes: Application to Gold-Catalyzed Oxyarylation of Alkenes

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 o...

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Published inOrganic letters Vol. 12; no. 21; pp. 4724 - 4727
Main Authors Ball, Liam T, Green, Michael, Lloyd-Jones, Guy C, Russell, Christopher A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.11.2010
Amer Chemical Soc
Subjects
Alkenes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Gold - chemistry
Kinetics
Molecular Structure
Oxidation-Reduction
Physical Sciences
Science & Technology
Silanes - chemistry
Stereoisomerism
HALIDES
AU(III)
COUPLING REACTIONS
COMPLEXES
GOLD(III)
ARYL
HETEROGENEOUS CATALYSTS
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Summary: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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ISSN:1523-7060
1523-7052
DOI:10.1021/ol1019162