Catalyst- and Reagent-Free Electrochemical Azole C-H Amination

Chemistry. 2018 Sep 3;24(49):12784-12789. doi: 10.1002/chem.201802832. Epub 2018 Aug 3.

Abstract

Catalyst- and chemical oxidant-free electrochemical azole C-H aminations were accomplished via cross-dehydrogenative C-H/N-H functionalization. The catalyst-free electrochemical C-H amination proved feasible on azoles with high levels of efficacy and selectivity, avoiding the use of stoichiometric oxidants under ambient conditions. Likewise, the C(sp3 )-H nitrogenation proved viable under otherwise identical conditions. The dehydrogenative C-H amination featured ample scope, including cyclic and acyclic aliphatic amines as well as anilines, and employed sustainable electricity as the sole oxidant.

Keywords: C−H amination; catalyst-free; electrochemistry; mild C−H functionalization; oxidant-free.