Fluorine chemistry has gained a lot of interest in the agrochemical, material, and pharmaceutical area due to the unique properties fluorine provides to organic molecules. Specifically, the trifluoromethoxy group (OCF3) is known to improve the bioavailability of compounds due to increased lipophilicity and high metabolic stability. Nucleophilic trifluoromethoxylation is a common method for installing the functional group, however, it is limited by the availability of trifluoromethoxide salts and the inherent decomposition of the OCF3 anion. To address some of these limitations, a new and isolable pyridinium trifluoromethoxide salt was synthesized from commercially available and inexpensive starting materials. This presentation will discuss the synthesis, isolation, structural characterization, and applications of this new trifluoromethoxide source in SN2 reactions to form trifluoromethyl ethers.

Development of practical pyridinium reagent for nucleophilic trifluoromethoxylation

ACS Spring Meeting 2021

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