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

[Image: see text] 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 employe...

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Detalles Bibliográficos
Autores principales: Kim, Sungjin, Khomutnyk, Yaroslav, Bannykh, Anton, Nagorny, Pavel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7783729/
https://www.ncbi.nlm.nih.gov/pubmed/33354969
http://dx.doi.org/10.1021/acs.orglett.0c03915
Descripción
Sumario:[Image: see text] 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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