Electrochemically promoted thio-Michael addition of N-substituted maleimides to thiols in an aqueous medium.

A stable and practical electrochemical method was developed to promote the thio-Michael addition of N-substituted maleimides to various thiols in an aqueous medium. This protocol was found to be excellent in terms of facile scale-up, oxidant- and catalyst-free conditions, broad substrate scopes, good functional group tolerance, and easily available substrates. Notably, a plausible reaction mechanism was derived from the results of a series of control experiments and CV studies, which indicated that a radical pathway might speed up the thio-Michael addition under constant current.