A Convenient Synthesis of Difluoroalkyl Ethers from Thionoesters Using Silver(I) Fluoride. Issue 70 (7th November 2019)

• Record Type: Journal Article
• Authors: Newton, Josiah; Driedger, Daniel; Nodwell, Matthew B.; Schaffer, Paul; Martin, Rainer E.; Britton, Robert; Friesen, Chadron M.
• Is Part Of: Chemistry. Volume 25:Issue 70(2019)
• Page Start: 15993
• Page End: 15997
• Publication Date: 2019-11-07
• Subjects: 18F-labelling -- difluoroether -- fluorodesulfurization -- radiotracer -- silver(I) fluoride; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201904132
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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 18 F‐labelled difluoroalkyl ethers using fluoride‐derived [ 18 F]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. Abstract : Mild at heart : A new method for the synthesis of difluoroalkyl ethers that involves the direct fluorodesulfurization of thionoesters with AgF at room temperature is reported (see scheme). This method should enable the synthesis of a wide range of difluoroalkyl ethers with applications in medicinal and materials chemistry, and radiotracer production.