Facile In Situ Difluoromethylation of Phenols and Thiols Using Ethyl Bromodifluoroacetate and K2CO3

Synlett DOI: 10.1055/s-0042-1751564 Herein, we report an efficient method to access difluoromethyl ethers of thiols and phenols using ethyl bromodifluoroacetate and K2CO3. This method demonstrates chemoselective difluoromethylation of thiols and phenols in the presence of amines. The current method also discloses the synthesis of bis(aryloxy)fluoromethane compounds which are least reported in the literature. Mechanistic investigations revealed that the reaction proceeds through a nucleophilic substitution pathway. We strongly believe this protocol would offer an efficient alternative to earlier photocatalyzed or radical-mediated difluoromethylation methods and it has a great potential in the scale-up of pharmaceutical and agrochemical intermediates that possess difluoromethyl group. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synlett - February 26, 2024 Category: Chemistry Authors: Dond, Bharat D. Chavan, Vijay P. Thore, Shivaji N. Tags: letter Source Type: research