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Synfacts 2006(4): 0343-0343  
DOI: 10.1055/s-2006-934342
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Hydrosilylation of Internal Alkynes

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
T. Sanada, T. Kato, M. Mitani, A. Mori*
Tokyo Institute of Technology, Japan
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Publication History

Publication Date:
24 March 2006 (online)

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Significance

Alkenyl silanes were shown to be useful intermediates and can react with transition-metal catalysts for C-C bond forming reactions. This report involves a very simple rhodium catalyst with low loading (0.25 mol%) that can affect hydrosilylation of internal alkynes. Unsymmetrical internal alkynes gave reasonable regioselectivity depending on the substituents. A nice one-pot procedure was shown to be very effective, producing the vinylsilane-fumarate adduct in 83% yield.