N-Aminophthalimide-mediated aerobic deborohydroxylation of boronic acid in air

Abstract

An efficient and convenient metal-free aerobic deborohydroxylation of boronic acids into phenols and alcohols in air is reported. The approach utilizes inexpensive and readily available N-aminophthalimide as a mediator to activate molecular oxygen, which enables the process to occur under relatively mild conditions. Due to the excellent chemoselectivity, the transformation tolerates various functional groups, especially oxidatively sensitive functionalities. Possible mechanisms are discussed based on primary experimental and theoretical mechanistic investigations.