Aromatic C–H amination in hexafluoroisopropanol

We report a direct radical aromatic amination reaction that provides unprotected anilines with an improvement in the substrate scope compared to prior art. Hydrogen bonding by the solvent hexafluoroisopropanol to anions of cationic species is responsible for increased reactivity and can rationalize...

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Detalles Bibliográficos
Autores principales: D'Amato, Erica M., Börgel, Jonas, Ritter, Tobias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6385662/
https://www.ncbi.nlm.nih.gov/pubmed/30881670
http://dx.doi.org/10.1039/c8sc04966a
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author D'Amato, Erica M.
Börgel, Jonas
Ritter, Tobias
author_facet D'Amato, Erica M.
Börgel, Jonas
Ritter, Tobias
author_sort D'Amato, Erica M.
collection PubMed
description We report a direct radical aromatic amination reaction that provides unprotected anilines with an improvement in the substrate scope compared to prior art. Hydrogen bonding by the solvent hexafluoroisopropanol to anions of cationic species is responsible for increased reactivity and can rationalize the enhancement in substrate scope. Our findings may have bearings on radical additions to arenes for direct C–H functionalization in general.
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spelling pubmed-63856622019-03-15 Aromatic C–H amination in hexafluoroisopropanol D'Amato, Erica M. Börgel, Jonas Ritter, Tobias Chem Sci Chemistry We report a direct radical aromatic amination reaction that provides unprotected anilines with an improvement in the substrate scope compared to prior art. Hydrogen bonding by the solvent hexafluoroisopropanol to anions of cationic species is responsible for increased reactivity and can rationalize the enhancement in substrate scope. Our findings may have bearings on radical additions to arenes for direct C–H functionalization in general. Royal Society of Chemistry 2019-01-11 /pmc/articles/PMC6385662/ /pubmed/30881670 http://dx.doi.org/10.1039/c8sc04966a Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
D'Amato, Erica M.
Börgel, Jonas
Ritter, Tobias
Aromatic C–H amination in hexafluoroisopropanol
title Aromatic C–H amination in hexafluoroisopropanol
title_full Aromatic C–H amination in hexafluoroisopropanol
title_fullStr Aromatic C–H amination in hexafluoroisopropanol
title_full_unstemmed Aromatic C–H amination in hexafluoroisopropanol
title_short Aromatic C–H amination in hexafluoroisopropanol
title_sort aromatic c–h amination in hexafluoroisopropanol
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6385662/
https://www.ncbi.nlm.nih.gov/pubmed/30881670
http://dx.doi.org/10.1039/c8sc04966a
work_keys_str_mv AT damatoericam aromaticchaminationinhexafluoroisopropanol
AT borgeljonas aromaticchaminationinhexafluoroisopropanol
AT rittertobias aromaticchaminationinhexafluoroisopropanol

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