Newton Josiah, Driedger Daniel, Nodwell Matthew B, Schaffer Paul, Martin Rainer E, Britton Robert, Friesen Chadron M
Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, V5A 1S6, Canada.
Department of Chemistry, Trinity Western University, Langley, British Columbia, V2Y 1Y1, Canada.
Chemistry. 2019 Dec 13;25(70):15993-15997. doi: 10.1002/chem.201904132. Epub 2019 Nov 7.
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 F-labelled difluoroalkyl ethers using fluoride-derived [ 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.
在此，我们报道了仅使用氟化银（I）对硫代酯进行温和且快速的氟脱硫反应。该反应表现出优异的官能团耐受性，补充了现有的二氟烷基醚合成策略，现有策略依赖于有毒且往往危险的试剂，这些试剂的官能团兼容性有限。我们还报道了将这一发现转化为使用氟化物衍生的[F]AgF生产F标记的二氟烷基醚。这一新方法应能实现多种二氟烷基醚的合成，其在药物化学、材料化学和放射性示踪剂生产中具有应用价值。
