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The first copper-catalyzed/promoted sp³-C Suzuki–Miyaura coupling reaction of gem-diborylalkanes with nonactivated electrophilic reagents is reported. Not only 1, 1-diborylalkanes but also some other gem-diborylalkanes can be coupled with nonactivated primary alkyl halides, offering a new method for sp³C–sp³C bond formation and, simultaneously, providing a new strategy for the synthesis of alkylboronic esters.