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Direct amidation of metallaaromatics: access to N-functionalized osmapentalynes via a 1,5-bromoamidated intermediate
The direct C–H amidation or imidation of metallaaromatics with N-bromoamides or imides has been achieved under mild conditions and leads to the formation of a family of N-functionalized metallapentalyne derivatives. A unique 1,5-bromoamidated species has been identified, and can be viewed as a σ(H)-...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8115065/ https://www.ncbi.nlm.nih.gov/pubmed/34084429 http://dx.doi.org/10.1039/d1sc01571k |
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author | Wang, Hongjian Ruan, Yonghong Lin, Yu-Mei Xia, Haiping |
author_facet | Wang, Hongjian Ruan, Yonghong Lin, Yu-Mei Xia, Haiping |
author_sort | Wang, Hongjian |
collection | PubMed |
description | The direct C–H amidation or imidation of metallaaromatics with N-bromoamides or imides has been achieved under mild conditions and leads to the formation of a family of N-functionalized metallapentalyne derivatives. A unique 1,5-bromoamidated species has been identified, and can be viewed as a σ(H)-adduct intermediate in a nucleophilic aromatic substitution. The 1,5-addition of both electrophilic and nucleophilic moieties into the metallaaromatic framework demonstrates a novel pathway in contrast to the typical radical process of arene C–H amidation involving N-haloamide reagents. |
format | Online Article Text |
id | pubmed-8115065 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-81150652021-06-02 Direct amidation of metallaaromatics: access to N-functionalized osmapentalynes via a 1,5-bromoamidated intermediate Wang, Hongjian Ruan, Yonghong Lin, Yu-Mei Xia, Haiping Chem Sci Chemistry The direct C–H amidation or imidation of metallaaromatics with N-bromoamides or imides has been achieved under mild conditions and leads to the formation of a family of N-functionalized metallapentalyne derivatives. A unique 1,5-bromoamidated species has been identified, and can be viewed as a σ(H)-adduct intermediate in a nucleophilic aromatic substitution. The 1,5-addition of both electrophilic and nucleophilic moieties into the metallaaromatic framework demonstrates a novel pathway in contrast to the typical radical process of arene C–H amidation involving N-haloamide reagents. The Royal Society of Chemistry 2021-04-07 /pmc/articles/PMC8115065/ /pubmed/34084429 http://dx.doi.org/10.1039/d1sc01571k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Wang, Hongjian Ruan, Yonghong Lin, Yu-Mei Xia, Haiping Direct amidation of metallaaromatics: access to N-functionalized osmapentalynes via a 1,5-bromoamidated intermediate |
title | Direct amidation of metallaaromatics: access to N-functionalized osmapentalynes via a 1,5-bromoamidated intermediate |
title_full | Direct amidation of metallaaromatics: access to N-functionalized osmapentalynes via a 1,5-bromoamidated intermediate |
title_fullStr | Direct amidation of metallaaromatics: access to N-functionalized osmapentalynes via a 1,5-bromoamidated intermediate |
title_full_unstemmed | Direct amidation of metallaaromatics: access to N-functionalized osmapentalynes via a 1,5-bromoamidated intermediate |
title_short | Direct amidation of metallaaromatics: access to N-functionalized osmapentalynes via a 1,5-bromoamidated intermediate |
title_sort | direct amidation of metallaaromatics: access to n-functionalized osmapentalynes via a 1,5-bromoamidated intermediate |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8115065/ https://www.ncbi.nlm.nih.gov/pubmed/34084429 http://dx.doi.org/10.1039/d1sc01571k |
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