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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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
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author Kim, Sungjin
Khomutnyk, Yaroslav
Bannykh, Anton
Nagorny, Pavel
author_facet Kim, Sungjin
Khomutnyk, Yaroslav
Bannykh, Anton
Nagorny, Pavel
author_sort Kim, Sungjin
collection PubMed
description [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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spelling pubmed-77837292021-01-06 Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride Kim, Sungjin Khomutnyk, Yaroslav Bannykh, Anton Nagorny, Pavel Org Lett [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. American Chemical Society 2020-12-23 2021-01-01 /pmc/articles/PMC7783729/ /pubmed/33354969 http://dx.doi.org/10.1021/acs.orglett.0c03915 Text en © 2020 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Kim, Sungjin
Khomutnyk, Yaroslav
Bannykh, Anton
Nagorny, Pavel
Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride
title Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride
title_full Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride
title_fullStr Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride
title_full_unstemmed Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride
title_short Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride
title_sort synthesis of glycosyl fluorides by photochemical fluorination with sulfur(vi) hexafluoride
url 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
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