S-, N-, and Se-difluoromethylation using sodium chlorodifluoroacetate

Org Lett. 2013 Oct 4;15(19):5036-9. doi: 10.1021/ol402370f. Epub 2013 Sep 23.

Abstract

A simple protocol for the difluoromethylation of thiols is reported using chlorodifluoroacetate as the difluoromethylating agent. This cheap reagent undergoes smooth decarboxylation at 95 °C to afford difluorocarbene, which can be trapped with a variety of aromatic and heteroaromatic thiols. The reaction is also effective for the difluoromethylation of heterocyclic nitrogen compounds and phenylselenol.