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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)-...

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Detalles Bibliográficos
Autores principales: Wang, Hongjian, Ruan, Yonghong, Lin, Yu-Mei, Xia, Haiping
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
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.
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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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