Open AccessSynthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride
Author(s) -
Sungjin Kim,
Yaroslav Khomutnyk,
Anton Bannykh,
Pavel Nagorny
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c03915
Subject(s) - chemistry , glycosyl , yield (engineering) , sulfur , photocatalysis , fluorine , sulfur hexafluoride , organic chemistry , combinatorial chemistry , catalysis , materials science , metallurgy
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.