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Nickel-Catalyzed Enantioselective Hydroboration of Vinylarenes

Hai N. Tran and Levi M. Stanley*

*Department of Chemistry, Iowa State University, Ames, Iowa 50011, United States, Email: lstanleyiastate.edu

H. N. Tran, L. M. Stanley, Org. Lett., 2022, 24, 395-399.

DOI: 10.1021/acs.orglett.1c04073


Abstract

A chiral nickel complex catalyzes a facile enantioselective hydroboration of vinylarenes to provide chiral benzylic boronate esters. Various vinylarenes react with bis(pinacolato)diboron in the presence of MeOH as a hydride source to form chiral boronate esters in good yields with high ee. Me4NF activates B2pin2 for ensuring fast transmetalation to achieve high enantioselectivities.

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proposed mechanism



Key Words

benzylic boronate esters


ID: J54-Y2022