Nickel-Catalyzed C(sp3)–C(sp3) Coupling of Cyclopropanols via α-Bimetalloid Radicals: Access to γ-Carbonyl gem-Bis(boronates) and gem-Silylboronate Esters

Herein, we disclose an efficient nickel-catalyzed C­(sp3)–C­(sp3) coupling reaction of ambiphilic reagents with cyclopropanols, enabling direct access to a range of synthetically valuable γ-carbonyl gem-diboronates and γ-carbonyl gem-silylboronate esters in good yields. This method shows broad substrate scope and excellent functional group tolerance for cyclopropanols. Mechanistic studies indicate the involvement of α-bimetalloid radicals, and the resulting Bpin groups in products offer versatile handles for further derivatization.