Department of Chemistry, University of Michigan, 930 N. University Ave., Ann Arbor, Michigan 48109, United States.
Org Lett. 2021 Jan 1;23(1):190-194. doi: 10.1021/acs.orglett.0c03915. Epub 2020 Dec 23.
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.
本研究描述了一种新的简便方法，使用六氟代硫酸作为廉价且安全的氟化试剂和 4,4'-二甲氧基二苯甲酮作为易得的有机光催化剂，通过光催化生成糖苷氟化物。该温和的方法用于生成 16 种不同的糖苷氟化物，包括具有酸和碱不稳定官能团的底物，产率为 43%-97%，并应用于连续流动中，在 7.7 克规模和 93%的产率下完成氟化。
