We describe a novel, regioselective alkylboration of versatile (hetero)benzylidenecyclopropanes with β-H-containing alkyl iodides and bis(pinacolato)diboron enabled by copper catalysis. This three-component method allows for consecutive B–Csp3 and Csp3–Csp3 bond formation to access Csp3-enriched diverse tertiary cyclopropyl boronic esters with broad functionality tolerance, and the so-formed C–B bond is amenable to further structural diversification. Radical clock experiment, Hammett analysis, and DFT calculation suggest a mechanism of polar, rather than radical manifold, and SN2-type C–C bond formation was found to be the rate-limiting step instead of migratory alkene insertion.
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Mondal et al. (2024) studied this question.
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