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Synthesis 2004(9): 1522-1526
DOI: 10.1055/s-2004-822405
DOI: 10.1055/s-2004-822405
PAPER
© Georg Thieme Verlag Stuttgart · New YorkStereoselective Synthesis of (Z)-1-Silyl-2-stannylethene by Palladium-Catalyzed Silastannation of Ethyne and Its Synthetic Transformations
Further Information
Received
16 April 2004
Publication Date:
08 June 2004 (online)
Publication History
Publication Date:
08 June 2004 (online)

Abstract
(Z)-1-Silyl-2-stannylethenes were stereoselectively synthesized by silastannation of ethyne, catalyzed by a palladium/tert-alkyl isocyanide catalyst, and the synthetic utilities were demonstrated by their transformations.
Key words
palladium - alkyne - silylstannane - cis-addition - cross-coupling
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References
The reaction failed to proceed effectively at room temperature.
10Interestingly, the reaction with trimethyl(dimethylphenyl-silyl)stannane in place of 1b gave no silastannation product at all. Instead, 1,2-diphenyltetramethyldisilane was formed by disproportionation.