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Synthesis of Secondary and Tertiary Alkylboranes via Formal Hydroboration of Terminal and 1,1-Disubstituted Alkenes

Hilary A. Kerchner and John Montgomery*

*Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, United States, Email: jmontgumich.edu

H. A. Kerchner, J. Montgomery, Org. Lett., 2016, 18, 5760-5763.

DOI: 10.1021/acs.orglett.6b03090 (free Supporting Information)


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Abstract

Cu-catalyzed formal hydroboration of terminal or 1,1-disubstituted alkenes with bis(pinacolato)diboron and methanol provides products with exceptional regiocontrol favoring the branched isomer. Subsequent photocatalytic cross-couplings using iridium and nickel cocatalysis enable a highly regioselective hydroarylation of terminal alkenes.

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Key Words

alkylboronates


ID: J54-Y2016