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. 2013;24(17):2177-2182.
doi: 10.1055/s-0033-1339795. Epub 2013 Sep 30.

Silyl-Heck Reactions for the Preparation of Unsaturated Organosilanes

Sara E S Martin  1 , Donald A Watson  1
Affiliations

Silyl-Heck Reactions for the Preparation of Unsaturated Organosilanes

Sara E S Martin et al. Synlett. 2013.

Abstract

Few methods exist to directly install silyl functionality onto olefins. This Synpacts highlights the state of the art of the silyl-Heck reaction and our recently developed conditions for preparing allyl and vinyl silanes from terminal alkenes using this method.

Keywords: alkene; allyl silane; palladium; silyl-Heck reaction; vinyl silane.

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Figures

Figure 1
Figure 1
Mechanistic Outline of the Silyl-Heck Reaction.
Scheme 1
Scheme 1
Oxidative Addition of Pt(0) Complexes to Si-X bonds.
Scheme 2
Scheme 2
Stoichiometric Reaction of 1 with Styrene.
Scheme 3
Scheme 3
First Example of A Silyl-Heck Reaction (Tanaka).
Scheme 4
Scheme 4
Improved Silyl-Heck Reaction (Watson).
Scheme 5
Scheme 5
Preparation of Vinyl Silanes Using the Silyl-Heck Reaction.
Scheme 6
Scheme 6
Conditions for Silyl-Heck Reaction Using TMSCl/LiI.
Scheme 7
Scheme 7
Preparation of Allyl Silanes Using the Silyl-Heck Reaction.
Scheme 8
Scheme 8
Formal C-H Functionalization Based Upon Silyl-Heck Reactions and Subsequent Functionalizations.
Scheme 9
Scheme 9
Murai’s Three-Component Couplings.
Scheme 10
Scheme 10
Kambe’s Zirconocene-Catalyzed Silylation of Alkenes.
See this image and copyright information in PMC

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