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A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry
The generation of aryl radicals from the corresponding halides by redox chemistry is generally considered a difficult task due to their highly negative reduction potentials. Here we demonstrate that α-aminoalkyl radicals can be used as both initiators and chain-carriers for the radical coupling of a...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8163300/ https://www.ncbi.nlm.nih.gov/pubmed/34094477 http://dx.doi.org/10.1039/d0sc04387g |
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author | Constantin, Timothée Juliá, Fabio Sheikh, Nadeem S. Leonori, Daniele |
author_facet | Constantin, Timothée Juliá, Fabio Sheikh, Nadeem S. Leonori, Daniele |
author_sort | Constantin, Timothée |
collection | PubMed |
description | The generation of aryl radicals from the corresponding halides by redox chemistry is generally considered a difficult task due to their highly negative reduction potentials. Here we demonstrate that α-aminoalkyl radicals can be used as both initiators and chain-carriers for the radical coupling of aryl halides with pyrrole derivatives, a transformation often employed to evaluate new highly reducing photocatalysts. This mode of reactivity obviates for the use of strong reducing species and was also competent in the formation of sp(2) C–P bonds. Mechanistic studies have delineated some of the key features operating that trigger aryl radical generation and also propagate the chain process. |
format | Online Article Text |
id | pubmed-8163300 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-81633002021-06-04 A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry Constantin, Timothée Juliá, Fabio Sheikh, Nadeem S. Leonori, Daniele Chem Sci Chemistry The generation of aryl radicals from the corresponding halides by redox chemistry is generally considered a difficult task due to their highly negative reduction potentials. Here we demonstrate that α-aminoalkyl radicals can be used as both initiators and chain-carriers for the radical coupling of aryl halides with pyrrole derivatives, a transformation often employed to evaluate new highly reducing photocatalysts. This mode of reactivity obviates for the use of strong reducing species and was also competent in the formation of sp(2) C–P bonds. Mechanistic studies have delineated some of the key features operating that trigger aryl radical generation and also propagate the chain process. The Royal Society of Chemistry 2020-10-20 /pmc/articles/PMC8163300/ /pubmed/34094477 http://dx.doi.org/10.1039/d0sc04387g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Constantin, Timothée Juliá, Fabio Sheikh, Nadeem S. Leonori, Daniele A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry |
title | A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry |
title_full | A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry |
title_fullStr | A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry |
title_full_unstemmed | A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry |
title_short | A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry |
title_sort | case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8163300/ https://www.ncbi.nlm.nih.gov/pubmed/34094477 http://dx.doi.org/10.1039/d0sc04387g |
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