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Synfacts 2009(9): 1012-1012  
DOI: 10.1055/s-0029-1217668
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Ketene Silyl Acetal Addition to Alkynes Gives Alkenylindiums

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
Y. Nishimoto, R. Moritoh, M. Yasuda, A. Baba*
Osaka University, Japan
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Publication History

Publication Date:
21 August 2009 (online)

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Significance

In previous work the authors have described InBr3-mediated reactions of silyl enolates with alkyl chlorides (Org. Lett. 2007, 9, 4931). In the present paper they present InBr3-promoted additions of ketene silyl acetals to alkynes to give alkenylindiums in high selectivities. Moreover, these in situ generated alkenylindiums could be coupled with iodobenzene using a palladium catalyst in one pot.