Cyclization of o-Allylstyrene via Hydrosilylation: Mechanistic Aspects of Hydrosilylation of Styrenes Catalyzed by Palladium−Phosphine Complexes
- 7 August 1998
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 63 (18) , 6137-6140
- https://doi.org/10.1021/jo980100b
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.Keywords
This publication has 19 references indexed in Scilit:
- Mechanistic Studies of Palladium(II)-Catalyzed Hydrosilation and Dehydrogenative Silation ReactionsJournal of the American Chemical Society, 1997
- Asymmetric Hydrosilylation of 1-Alkenes Catalyzed by Palladium–MOPBulletin of the Chemical Society of Japan, 1995
- A New Reactive System for Catalytic Bis-Silylation of Acetylenes and OlefinsOrganometallics, 1994
- Mechanism of a cobalt(III)-catalyzed olefin hydrosilation reaction: direct evidence for a silyl migration pathwayJournal of the American Chemical Society, 1993
- Silafunctional compounds in organic synthesis. 35. Silafunctional .alpha.,.beta.-epoxy silanes. Transformation into erythro- and threo-1,2-diol skeletons and its application to the synthesis of (.+-.)-exo-brevicominThe Journal of Organic Chemistry, 1987
- HomophthalaldehydeSynthesis, 1971
- Dicobalt Octacarbonyl as a Catalyst for Hydrosilation of OlefinsJournal of the American Chemical Society, 1965
- Homogeneous Catalysis. II. The Mechanism of the Hydrosilation of Olefins Catalyzed by Group VIII Metal Complexes1Journal of the American Chemical Society, 1965
- The Addition of Silicon Hydrides to Olefinic Double Bonds. VIII. The Addition of Trichlorosilane-dJournal of the American Chemical Society, 1964
- Reaktionen mit Phosphin‐alkylenen, VII. Olefine und Ketone durch Autoxydation von Phosphin‐alkylenenEuropean Journal of Inorganic Chemistry, 1963