A Light-Promoted Innate Trifluoromethylation of Pyridones and Related N-Heteroarenes

[Image: see text] We report a practical, light-mediated perfluoroalkylation using Langlois’ reagent (sodium trifluoromethylsulfinate) that proceeds in the absence of any photocatalyst or additives. This method has allowed for the facile functionalization of pyridones and related N-heteroarenes such...

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Autores principales: Dang-Nguyen, Ashley, Legaspi, Kristine C., McCarty, Connor T., Smith, Diane K., Gustafson, Jeffrey
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10334463/
https://www.ncbi.nlm.nih.gov/pubmed/37377204
http://dx.doi.org/10.1021/acs.orglett.3c01710
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author Dang-Nguyen, Ashley
Legaspi, Kristine C.
McCarty, Connor T.
Smith, Diane K.
Gustafson, Jeffrey
author_facet Dang-Nguyen, Ashley
Legaspi, Kristine C.
McCarty, Connor T.
Smith, Diane K.
Gustafson, Jeffrey
author_sort Dang-Nguyen, Ashley
collection PubMed
description [Image: see text] We report a practical, light-mediated perfluoroalkylation using Langlois’ reagent (sodium trifluoromethylsulfinate) that proceeds in the absence of any photocatalyst or additives. This method has allowed for the facile functionalization of pyridones and related N-heteroarenes such as azaindole. This protocol is operationally simple, uses readily available materials, and is tolerable for electron-neutral and -rich functional pyridones. Cyclic voltammetry was utilized as a mechanistic probe, and preliminary data suggest the reaction may involve an electrophilic radical mechanism.
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spelling pubmed-103344632023-07-12 A Light-Promoted Innate Trifluoromethylation of Pyridones and Related N-Heteroarenes Dang-Nguyen, Ashley Legaspi, Kristine C. McCarty, Connor T. Smith, Diane K. Gustafson, Jeffrey Org Lett [Image: see text] We report a practical, light-mediated perfluoroalkylation using Langlois’ reagent (sodium trifluoromethylsulfinate) that proceeds in the absence of any photocatalyst or additives. This method has allowed for the facile functionalization of pyridones and related N-heteroarenes such as azaindole. This protocol is operationally simple, uses readily available materials, and is tolerable for electron-neutral and -rich functional pyridones. Cyclic voltammetry was utilized as a mechanistic probe, and preliminary data suggest the reaction may involve an electrophilic radical mechanism. American Chemical Society 2023-06-28 /pmc/articles/PMC10334463/ /pubmed/37377204 http://dx.doi.org/10.1021/acs.orglett.3c01710 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Dang-Nguyen, Ashley
Legaspi, Kristine C.
McCarty, Connor T.
Smith, Diane K.
Gustafson, Jeffrey
A Light-Promoted Innate Trifluoromethylation of Pyridones and Related N-Heteroarenes
title A Light-Promoted Innate Trifluoromethylation of Pyridones and Related N-Heteroarenes
title_full A Light-Promoted Innate Trifluoromethylation of Pyridones and Related N-Heteroarenes
title_fullStr A Light-Promoted Innate Trifluoromethylation of Pyridones and Related N-Heteroarenes
title_full_unstemmed A Light-Promoted Innate Trifluoromethylation of Pyridones and Related N-Heteroarenes
title_short A Light-Promoted Innate Trifluoromethylation of Pyridones and Related N-Heteroarenes
title_sort light-promoted innate trifluoromethylation of pyridones and related n-heteroarenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10334463/
https://www.ncbi.nlm.nih.gov/pubmed/37377204
http://dx.doi.org/10.1021/acs.orglett.3c01710
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