A successful collaboration between the Hartwig Lab and Pfizer Medicinal Chemistry has resulted in a new method for the synthesis of aryl- and heteroaryl-trifluoromethyl ethers. There are relatively few established methods for the construction of aryl-trifluoromethyl ethers from phenols. Those that do exist proceed with very narrow substrate scope and rarely occur when heteroaromatic moieties are present. We report a two-step, metal-free, trifluoromethylation of aromatic and heteroaromatic alcohols via the intermediacy of aryl and heteroaryl xanthates, respectively. Utilizing a newly-developed xanthalating reagent, a variety of xanthates react under mild reaction conditions, with no strict moisture or atmospheric controls, to form the corresponding aryl and heteroaryl trifluoromethyl ethers. Reaction optimization and the workings of a successful collaboration will be discussed.

Metal-free trifluoromethylation of phenols via xanthates: New synthesis of aryl and heteroaryl-trifluoromethyl ethers

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.