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Synfacts 2005(1): 0121-0121  
DOI: 10.1055/s-2005-872208
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Tetraorganosilicon Reagents for Cross-Coupling Reactions

Contributor(s): Victor Snieckus, Farhad Nowrouzi
Y. Nakao*, H. Imanaka, A. K. Sahoo, A. Yada, T. Hiyama*
Kyoto University, Japan
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Publication History

Publication Date:
21 September 2005 (online)

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Significance

The readily accessible and highly stable alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes undergo cross-coupling with aryl and alkenyl iodides under mild conditions in a reaction of broad scope (32 examples) and excellent yields (73-99%). The reaction is adaptable to gram scale, and the cyclic silyl ether is recovered and reused. The latter aspect is the first such demonstration for a cross-coupling reaction.