Cyclization of O-Allylstyrene Via Hydrosilylation: Mechanistic Aspects of Hydrosilylation of Styrenes Catalyzed by Palladium-Phosphine Complexes

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2001 Oct 24

PMID 11672242

Citations 5

Authors

Yasuhiro Uozumi

Hayato Tsuji

Tamio Hayashi

Affiliations

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Abstract

Hydrosilylation of o-allylstyrene with trichlorosilane in the presence of 0.3 mol % of a palladium catalyst bearing triphenylphosphine gave trans-1-methyl-2-(trichlorosilylmethyl)indan, 1-(2-(2-propenyl)phenyl)-1-trichlorosilylethane, and 1-(2-((E)-1-propenyl)phenyl)-1-trichlorosilylethane. The reaction of styrene with trichlorosilane gave a quantitative yield of 1-phenyl-1-(trichlorosilyl)ethane while allylbenzene did not give silylation products under the same reaction conditions. These results show that the hydropalladation process is operative in the hydrosilylation of styrene derivatives with trichlorosilane catalyzed by palladium-phosphine complexes.

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