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Regioselective Hydroalkylation of Vinyl- and Allylsilanes as Well as Vinylgermanes under Ni-H Catalysis

Daniel Brösamlen and Martin Oestreich*

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

D. Brösamlen, M. Oestreich, Org. Lett., 2023, 25, 5319-5323.

DOI: 10.1021/acs.orglett.3c01881


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Abstract

A Ni-H-catalyzed hydroalkylation of vinylsilanes and -germanes as well as allylsilanes with unactivated alkyl iodides proceeds with anti-Markovnikov selectivity to deliver the linear regioisomer. Mechanistic control experiments support a radical mechanism, and a competition experiment reveals that the chemoselectivity is in favor of the vinyl over the allyl group.

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Copper-Catalyzed Cross-Coupling of Vinyliodonium Salts and Zinc-Based Silicon Nucleophiles

L. Zhang, M. Oestreich, Org. Lett., 2018, 20, 8061-8063.


Key Words

alkylsilanes, DEMS


ID: J54-Y2023