Issue 2, 2017

Transition-metal free direct difluoromethylthiolation of electron-rich aromatics with difluoromethanesulfonyl chloride

Abstract

A new method for phosphine-mediated difluoromethylthiolation of indole derivatives and other electron-rich aromatics including pyrroles, pyrazolones, indolizine, and 1,3,5-trimethoxybenzene was developed using difluoromethanesulfonyl chloride. The additive n-Bu4NI was demonstrated to facilitate this reaction by generating iodine in situ, which could promote this transformation. The use of a transition-metal-free protocol, readily available reagents, and mild reaction conditions makes this protocol more practical than traditional methods.

Graphical abstract: Transition-metal free direct difluoromethylthiolation of electron-rich aromatics with difluoromethanesulfonyl chloride

Supplementary files

Article information

Article type
Research Article
Submitted
26 Sep 2016
Accepted
22 Nov 2016
First published
23 Nov 2016

Org. Chem. Front., 2017,4, 232-235

Transition-metal free direct difluoromethylthiolation of electron-rich aromatics with difluoromethanesulfonyl chloride

X. Zhao, A. Wei, T. Li, Z. Su, J. Chen and K. Lu, Org. Chem. Front., 2017, 4, 232 DOI: 10.1039/C6QO00581K

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