Deboronative functionalization of alkylboron species via a radical-transfer strategy

Abstract

With advances in organoboron chemistry, boron-centered functional groups have become increasingly attractive. In particular, alkylboron species are highly versatile reagents for organic synthesis, but the direct generation of alkyl radicals from commonly used, bench-stable boron species has not been thoroughly investigated. Herein, we describe a method for activating C–B bonds by nitrogen- or oxygen-radical transfer that is applicable to alkylboronic acids and esters and can be used for both Michael addition reactions and Minisci reactions to generate alkyl or arylated products.