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

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.

Automated summary

This study introduces a new convenient method for the photocatalytic generation of glycosyl fluorides using sulfur(VI) hexafluoride and 4,4'-dimethoxybenzophenone. The mild method is able to generate 16 different glycosyl fluorides with yields ranging from 43% to 97% and can be applied on a large scale with high yield in continuous flow synthesis.