Access to Diverse Organoborons by α-Deprotonation and Functionalization of Benzylboronates

Abstract

Described here is a simple and efficient method to prepare organoboron compounds through α-deprotonation and functionalization of benzylboronates. In addition to alkyl halides, chlorosilane, deuterium oxide, and trifluoromethyl alkene could also serve as electrophiles in this approach. Notably, the boryl group enables high diastereoselectivities when unsymmetrical secondary α-bromoesters are used. This methodology exhibits a broad substrate scope and high atomic efficiency and offers an alternative C-C bond disconnection for the synthesis of benzylboronates.

Topics & Concepts