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Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride

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journal contribution
posted on 23.12.2020, 13:05 by Sungjin Kim, Yaroslav Khomutnyk, Anton Bannykh, Pavel Nagorny
This study describes a new convenient method for the photocatalytic generation of glycosyl fluorides using sulfur­(VI) hexafluoride as an inexpensive and safe fluorinating agent and 4,4′-dimethoxybenzophenone as a readily available organic photocatalyst. This mild method was employed to generate 16 different glycosyl fluorides, including the substrates with acid and base labile functionalities, in yields of 43%–97%, and it was applied in continuous flow to accomplish fluorination on an 7.7 g scale and 93% yield.