Radical generation from electroreduction of aryl and benzyl ammonium salts: synthesis of organoboronates

Abstract

We report a direct electrocatalytic borylation of aryl and benzyl trimethylammonium salts with bis(pinacolato)diboron at room temperature. The protocol is compatible with substrates bearing a variety of functional groups, including halides (Cl and Br), which are not tolerated by previously reported methods involving nickel catalysis or photocatalysis. The protocol does not require stoichiometric metals, external reducing agents, or sacrificial anodes and can be carried out on a gram scale.