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Copper-Catalyzed Double C(sp3)-Si Coupling of Geminal Dibromides: Ionic-to-Radical Switch in the Reaction Mechanism

Hamideh Hazrati, Martin Oestreich*

*Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin, Germany, Email:

H. Hazrati, M. Oestreich, Org. Lett., 2018, 20, 5367-5369.

DOI: 10.1021/acs.orglett.8b02281 (free Supporting Information)

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The conversion of geminal dibromides into 1,1-disilylated alkanes in the presence of a Si-B reagent as the silicon pronucleophile is promoted by a copper(I) catalyst generated in situ from CuBr·SMe2 and 4,4′-di-tert-butyl-2,2′-bipyridine. The two C(sp3)-Si bond-forming events differ in mechanism, with the first being ionic and the second being radical.

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ID: J54-Y2018