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

Sungjin Kim | Zendy; Yaroslav Khomutnyk | Zendy; Anton Bannykh | Zendy; Pavel Nagorny | Zendy

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Synthesis 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 , sulfur hexafluoride , fluorine , photocatalysis , 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.

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