A Convenient Synthesis of Difluoroalkyl Ethers from Thionoesters Using Silver(I) Fluoride.

Newton, Josiah; Driedger, Daniel; Nodwell, Matthew B.; Schaffer, Paul; Martin, Rainer E.; Britton, Robert; Friesen, Chadron M.

Herein we report the mild and rapid fluorodesulfurization of thionoesters using only silver(I) fluoride. This reaction demonstrates excellent functional group tolerance and complements existing strategies for difluoroalkyl ether synthesis, which rely on toxic and often dangerous reagents that demonstrate limited functional group compatibility. We additionally report the translation of this finding to the production of 18F‐labelled difluoroalkyl ethers using fluoride‐derived [18F]AgF. This new process should enable the synthesis of a wide range of difluoroalkyl ethers with applications in medicinal and materials chemistry, and radiotracer production.

ETHER synthesis; RADIOACTIVE tracers; SILVER; FLUORIDES; FUNCTIONAL groups; PHARMACEUTICAL chemistry

Chemistry - A European Journal, 2019, Vol 25, Issue 70, p15993

0947-6539

Academic Journal

10.1002/chem.201904132