Olefin isomerization and hydrosilylation catalysis by lewis acidic organofluorophosphonium salts

Manuel Pérez, Lindsay J. Hounjet, Christopher B. Caputo, Roman Dobrovetsky, Douglas W. Stephan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Organofluorophosphonium salts of the formula [(C6F 5)3-xPhxPF][B(C6F5) 4] (x = 0, 1) exhibit Lewis acidity derived from a low-lying σ* 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.

Original languageEnglish
Pages (from-to)18308-18310
Number of pages3
JournalJournal of the American Chemical Society
Volume135
Issue number49
DOIs
StatePublished - 11 Dec 2013
Externally publishedYes

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