Diastereoselective Hydrodifluoromethylation of Alkenyl -Heterocycles via Photocatalytic Radical-Polar Crossover.

J Org Chem

Xenon Pharmaceuticals Inc., 3650 Gilmore Way, Burnaby, British Columbia, Canada, V5G 4W8.

Published: November 2024

A diastereoselective hydrodifluoromethylation of -heteroaryl alkenes was successfully established. This method was applicable to an array of -heteroaryl substrates with both cyclic and acyclic alkenes while displaying tolerance to a variety of functional groups. The conditions were also expanded to obtain hydrotrifluoromethylated products with similar results. Initial mechanistic studies suggest that the final protonation step is accessed through a radical-polar crossover process.

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http://dx.doi.org/10.1021/acs.joc.4c02169DOI Listing

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