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Chlorination of arenes via the degradation of toxic chlorophenols

Aryl chlorides are among the most versatile synthetic precursors, and yet inexpensive and benign chlorination techniques to produce them are underdeveloped. We propose a process to generate aryl chlorides by chloro-group transfer from chlorophenol pollutants to arenes during their mineralization, ca...

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Detalles Bibliográficos
Autores principales: Liu, Mingyang, Yang, Xuemei, Dyson, Paul J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: National Academy of Sciences 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9173806/
https://www.ncbi.nlm.nih.gov/pubmed/35588450
http://dx.doi.org/10.1073/pnas.2122425119
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author Liu, Mingyang
Yang, Xuemei
Dyson, Paul J.
author_facet Liu, Mingyang
Yang, Xuemei
Dyson, Paul J.
author_sort Liu, Mingyang
collection PubMed
description Aryl chlorides are among the most versatile synthetic precursors, and yet inexpensive and benign chlorination techniques to produce them are underdeveloped. We propose a process to generate aryl chlorides by chloro-group transfer from chlorophenol pollutants to arenes during their mineralization, catalyzed by Cu(NO(3))(2)/NaNO(3) under aerobic conditions. A wide range of arene substrates have been chlorinated using this process. Mechanistic studies show that the Cu catalyst acts in cooperation with NO(x) species generated from the decomposition of NaNO(3) to regulate the formation of chlorine radicals that mediate the chlorination of arenes together with the mineralization of chlorophenol. The selective formation of aryl chlorides with the concomitant degradation of toxic chlorophenol pollutants represents a new approach in environmental pollutant detoxication. A reduction in the use of traditional chlorination reagents provides another (indirect) benefit of this procedure.
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spelling pubmed-91738062022-06-08 Chlorination of arenes via the degradation of toxic chlorophenols Liu, Mingyang Yang, Xuemei Dyson, Paul J. Proc Natl Acad Sci U S A Physical Sciences Aryl chlorides are among the most versatile synthetic precursors, and yet inexpensive and benign chlorination techniques to produce them are underdeveloped. We propose a process to generate aryl chlorides by chloro-group transfer from chlorophenol pollutants to arenes during their mineralization, catalyzed by Cu(NO(3))(2)/NaNO(3) under aerobic conditions. A wide range of arene substrates have been chlorinated using this process. Mechanistic studies show that the Cu catalyst acts in cooperation with NO(x) species generated from the decomposition of NaNO(3) to regulate the formation of chlorine radicals that mediate the chlorination of arenes together with the mineralization of chlorophenol. The selective formation of aryl chlorides with the concomitant degradation of toxic chlorophenol pollutants represents a new approach in environmental pollutant detoxication. A reduction in the use of traditional chlorination reagents provides another (indirect) benefit of this procedure. National Academy of Sciences 2022-05-19 2022-05-24 /pmc/articles/PMC9173806/ /pubmed/35588450 http://dx.doi.org/10.1073/pnas.2122425119 Text en Copyright © 2022 the Author(s). Published by PNAS. https://creativecommons.org/licenses/by/4.0/This open access article is distributed under Creative Commons Attribution License 4.0 (CC BY) (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Physical Sciences
Liu, Mingyang
Yang, Xuemei
Dyson, Paul J.
Chlorination of arenes via the degradation of toxic chlorophenols
title Chlorination of arenes via the degradation of toxic chlorophenols
title_full Chlorination of arenes via the degradation of toxic chlorophenols
title_fullStr Chlorination of arenes via the degradation of toxic chlorophenols
title_full_unstemmed Chlorination of arenes via the degradation of toxic chlorophenols
title_short Chlorination of arenes via the degradation of toxic chlorophenols
title_sort chlorination of arenes via the degradation of toxic chlorophenols
topic Physical Sciences
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9173806/
https://www.ncbi.nlm.nih.gov/pubmed/35588450
http://dx.doi.org/10.1073/pnas.2122425119
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AT yangxuemei chlorinationofarenesviathedegradationoftoxicchlorophenols
AT dysonpaulj chlorinationofarenesviathedegradationoftoxicchlorophenols