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A Convenient Synthesis of Difluoroalkyl Ethers from Thionoesters Using Silver(I) Fluoride
Author(s) -
Newton Josiah,
Driedger Daniel,
Nodwell Matthew B.,
Schaffer Paul,
Martin Rainer E.,
Britton Robert,
Friesen Chadron M.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904132
Subject(s) - fluoride , reagent , ether , functional group , chemistry , combinatorial chemistry , compatibility (geochemistry) , organic chemistry , chemical engineering , inorganic chemistry , engineering , polymer
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.