Visible light initiated amino group <i>ortho</i>-directed copper(<scp>i</scp>)-catalysed aerobic oxidative C(sp)–S coupling reaction: synthesis of substituted 2-phenylbenzothiazoles <i>via</i> thia-Wolff rearrangement

Abstract

A facile amino group ortho-directed visible-light-driven copper-catalysed aerobic oxidative C(sp)-S coupling reaction of a dimer of 2-aminothiophenol with terminal alkynes was achieved. This photochemical reaction shows an excellent conversion and chemoselectivity towards the formation of C(sp)-S coupling and has been employed for a wide range of thiol dimers, and alkynes. Furthermore, the synthetic utility of the synthesized alkynyl sulfides was demonstrated as a direct method for the construction of 2-phenylbenzothiazoles from the corresponding alkynyl sulfides via "thia-Wolff rearrangement" using AgNO3 and visible light using 9-mesityl-10-methylacridinium ions (Acr+-Mes) as photoredox catalyst system.