Synthesis of Fluorinated Amide Derivatives via a Radical N-Perfluoroalkylation–Defluorination Pathway

[Image: see text] A one-pot approach to fluorinated hydroxamic acid, amide, and thioamide derivatives is reported. The reaction proceeds via an N-perfluoroalkylation of nitrosoarenes with perfluoroalkanesulfinates, resulting in labile N-perfluoroalkylated hydroxylamines. By the addition of suitable...

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Autores principales: Zheng, Zhiyao, van der Werf, Angela, Deliaval, Marie, Selander, Nicklas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7311088/
https://www.ncbi.nlm.nih.gov/pubmed/32208612
http://dx.doi.org/10.1021/acs.orglett.0c00768
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author Zheng, Zhiyao
van der Werf, Angela
Deliaval, Marie
Selander, Nicklas
author_facet Zheng, Zhiyao
van der Werf, Angela
Deliaval, Marie
Selander, Nicklas
author_sort Zheng, Zhiyao
collection PubMed
description [Image: see text] A one-pot approach to fluorinated hydroxamic acid, amide, and thioamide derivatives is reported. The reaction proceeds via an N-perfluoroalkylation of nitrosoarenes with perfluoroalkanesulfinates, resulting in labile N-perfluoroalkylated hydroxylamines. By the addition of suitable additives, a controllable oxy/thiodefluorination of the fluorinated hydroxylamine intermediates was achieved. The method highlights N-perfluoroalkylated amines as versatile intermediates for further synthesis.
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spelling pubmed-73110882020-06-24 Synthesis of Fluorinated Amide Derivatives via a Radical N-Perfluoroalkylation–Defluorination Pathway Zheng, Zhiyao van der Werf, Angela Deliaval, Marie Selander, Nicklas Org Lett [Image: see text] A one-pot approach to fluorinated hydroxamic acid, amide, and thioamide derivatives is reported. The reaction proceeds via an N-perfluoroalkylation of nitrosoarenes with perfluoroalkanesulfinates, resulting in labile N-perfluoroalkylated hydroxylamines. By the addition of suitable additives, a controllable oxy/thiodefluorination of the fluorinated hydroxylamine intermediates was achieved. The method highlights N-perfluoroalkylated amines as versatile intermediates for further synthesis. American Chemical Society 2020-03-25 2020-04-03 /pmc/articles/PMC7311088/ /pubmed/32208612 http://dx.doi.org/10.1021/acs.orglett.0c00768 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Zheng, Zhiyao
van der Werf, Angela
Deliaval, Marie
Selander, Nicklas
Synthesis of Fluorinated Amide Derivatives via a Radical N-Perfluoroalkylation–Defluorination Pathway
title Synthesis of Fluorinated Amide Derivatives via a Radical N-Perfluoroalkylation–Defluorination Pathway
title_full Synthesis of Fluorinated Amide Derivatives via a Radical N-Perfluoroalkylation–Defluorination Pathway
title_fullStr Synthesis of Fluorinated Amide Derivatives via a Radical N-Perfluoroalkylation–Defluorination Pathway
title_full_unstemmed Synthesis of Fluorinated Amide Derivatives via a Radical N-Perfluoroalkylation–Defluorination Pathway
title_short Synthesis of Fluorinated Amide Derivatives via a Radical N-Perfluoroalkylation–Defluorination Pathway
title_sort synthesis of fluorinated amide derivatives via a radical n-perfluoroalkylation–defluorination pathway
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7311088/
https://www.ncbi.nlm.nih.gov/pubmed/32208612
http://dx.doi.org/10.1021/acs.orglett.0c00768
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AT deliavalmarie synthesisoffluorinatedamidederivativesviaaradicalnperfluoroalkylationdefluorinationpathway
AT selandernicklas synthesisoffluorinatedamidederivativesviaaradicalnperfluoroalkylationdefluorinationpathway

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