Regioselective C-H Phosphorothiolation of (Hetero)arenes Enabled by the Synergy of Electrooxidation and Ultrasonic Irradiation

Org Lett. 2021 Jun 4;23(11):4214-4218. doi: 10.1021/acs.orglett.1c01161. Epub 2021 May 13.

Abstract

An electrochemically regioselective C-H phosphorothiolation of (hetero)arenes with thiocyanate as the S source under ultrasonic irradiation has been developed. The synergistic cooperation of electrooxidation and ultrasonication markedly accelerated the C-H phosphorothiolation reaction. This mechanistically different method is distinguished by its wide substrate scope and transition-metal-free and external-oxidant-free conditions, thus complementing the existing metal-catalyzed or peroxide-mediated protocols for the green synthesis of S-(hetero)aryl phosphorothioates.

Publication types

  • Research Support, Non-U.S. Gov't