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Issue 26, 2020
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Visible light initiated amino group ortho-directed copper(i)-catalysed aerobic oxidative C(sp)–S coupling reaction: synthesis of substituted 2-phenylbenzothiazoles via thia-Wolff rearrangement

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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.

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

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Article information


Submitted
31 Jan 2020
Accepted
24 Feb 2020
First published
26 Feb 2020

Chem. Commun., 2020,56, 3781-3784
Article type
Communication

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

M. B. Reddy and R. Anandhan, Chem. Commun., 2020, 56, 3781
DOI: 10.1039/D0CC00815J

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