Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 49, Pages 18308-18310Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja410379x
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Funding
- NSERC of Canada
- Canada Research Chair
- NSERC of Canada CGS-D
- Walter C. Sumner Fellowship
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Organofluorophosphonium salts of the formula [(C6F5)(3-x)PhxPF][B(C6F5)(4)] (x = 0, 1) exhibit Lewis acidity derived from a low-lying sigma* orbital at P opposite F. This acidity is evidenced by the reactions of these salts with olefins, which catalyze the rapid isomerization of 1-hexene to 2-hexene, the cationic polymerization of isobutylene, and the Friedel Crafts-type dimerization of 1,1-diphenylethylene. In the presence of hydrosilanes, olefins and alkynes undergo efficient hydrosilylation catalysis to the alkylsilanes. Experimental and computational considerations of the mechanism are consistent with the sequential activation and 1,2-addition of hydrosilane across the unsaturated C-C bonds.
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