Copper(I)-Catalyzed Regio- and Chemoselective Single and Double Addition of Nucleophilic Silicon to Propargylic Chlorides and Phosphates

Chinmoy K. Hazra and Martin Oestreich*

*Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin, Germany, Email: martin.oestreichtu-berlin.de

C. K. Hazra, M. Oestreich, Org. Lett., 2012, 14, 4010-4013.

DOI: 10.1021/ol301827t

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Abstract

Copper(I)-catalyzed propargylic substitution of linear precursors with one equivalent of (Me₂PhSi)₂Zn predominantly yields the γ isomer independent of the propargylic leaving group. The formed allenylic silane can regioselectively react with a second equivalent of (Me₂PhSi)₂Zn to give a bifunctional building block with allylic and vinylic silicon groups. The propargylic displacement occurs quantitatively prior to the addition step.

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Key Words

vinylsilanes, allylsilanes

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ID: J54-Y2012-2490