Nickel-catalyzed synthesis of 1,1-diborylalkanes from terminal alkenes

Abstract

Organoboron compounds play an irreplaceable role in synthetic chemistry and the related transformations based on the unique reactivity of C-B bond are potentially the most efficient methods for the synthesis of organic molecules. The synthetic importance of multiboron compounds in C-C bond formation and function transformation reactions is growing and the related borations of activated or nonactivated alkenes have been developed recently. However, introducing directly two boron moieties into the terminal sites of alkenes giving 1,1-diborylalkanes in a catalytic fashion has not been explored yet. Here we describe a synthetic strategy of 1,1-diborylalkanes via a Ni-catalyzed 1,1-diboration of readily available terminal alkenes. This methodology shows high level of chemoselectivity and regioselectivity and can be used to convert a large variety of terminal alkenes, such as vinylarenes, aliphatic alkenes and lower alkenes, to 1,1-diborylalkanes.