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Palladium-Catalyzed Regio- and Stereoselective Hydrosilylation of Electron-Deficient Alkynes

Yuto Sumida*, Tomoe Kato, Suguru Yoshida and Takamitsu Hosoya*

*Institute of Biomaterials and Bioengineerings, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan, Email: sumida.cbtmd.ac.jp, thosoya.cbtmd.ac.jp

Y. Sumida, T. Kato, S. Yoshida, T. Hosoya, Org. Lett., 2012, 14, 1552-1555.

DOI: 10.1021/ol300279c (free Supporting Information)


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Abstract

Palladium catalyzes a highly regio- and stereoselective hydrosilylation applicable to a broad range of electron-deficient alkynes. The resulting α-silylalkenes can be further transformated using particularly Hiyama coupling and stereoinverting iododesilylation followed by Suzuki-Miyaura coupling, which enables stereodivergent syntheses of α-arylenoates.

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Key Words

vinylsilanes, vinylsiloxanes


ID: J54-Y2012-0820