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Published on: January 19, 2016
A Convenient Synthesis of Difluoroalkyl Ethers from Thionoesters Using Silver(I) Fluoride
Josiah Newton1,2, Daniel Driedger2, Matthew B Nodwell1
1Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada.
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.
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