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Updated: May 26, 2025

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Nickel-Catalyzed Branched Hydroalkylation of Alkenes with Diazo Compounds

Nikita Kvasovs1, Valeriia Iziumchenko1, Alistair J Sterling1

  • 1Department of Chemistry and Biochemistry, The University of Texas at Dallas, 800 West Campbell Road, Richardson, Texas 75080-3021, United Sates.

Journal of the American Chemical Society
|February 25, 2025
PubMed

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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