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Efficient synthesis of primary and secondary amides via reacting esters with alkali metal amidoboranes
Amides are one of the most important organic compounds that are widely applied in medicine, biochemistry, and materials science. To find an efficient synthetic method of amides is a challenge for organic chemistry. We report here a facile synthesis method of primary and secondary amides through a di...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8514480/ https://www.ncbi.nlm.nih.gov/pubmed/34645807 http://dx.doi.org/10.1038/s41467-021-25836-5 |
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author | Guo, Yu Wang, Ruo-Ya Kang, Jia-Xin Ma, Yan-Na Xu, Cong-Qiao Li, Jun Chen, Xuenian |
author_facet | Guo, Yu Wang, Ruo-Ya Kang, Jia-Xin Ma, Yan-Na Xu, Cong-Qiao Li, Jun Chen, Xuenian |
author_sort | Guo, Yu |
collection | PubMed |
description | Amides are one of the most important organic compounds that are widely applied in medicine, biochemistry, and materials science. To find an efficient synthetic method of amides is a challenge for organic chemistry. We report here a facile synthesis method of primary and secondary amides through a direct amidation of esters with sodium amidoboranes (NaNHRBH(3), R = H, Me), at room temperature without using catalysts and other reagents. This process is rapid and chemoselective, and features quantitative conversion and wide applicability for esters tolerating different functional groups. The experimental and theoretical studies reveal a reaction mechanism with nucleophilic addition followed by a swift proton transfer-induced elimination reaction. |
format | Online Article Text |
id | pubmed-8514480 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-85144802021-10-29 Efficient synthesis of primary and secondary amides via reacting esters with alkali metal amidoboranes Guo, Yu Wang, Ruo-Ya Kang, Jia-Xin Ma, Yan-Na Xu, Cong-Qiao Li, Jun Chen, Xuenian Nat Commun Article Amides are one of the most important organic compounds that are widely applied in medicine, biochemistry, and materials science. To find an efficient synthetic method of amides is a challenge for organic chemistry. We report here a facile synthesis method of primary and secondary amides through a direct amidation of esters with sodium amidoboranes (NaNHRBH(3), R = H, Me), at room temperature without using catalysts and other reagents. This process is rapid and chemoselective, and features quantitative conversion and wide applicability for esters tolerating different functional groups. The experimental and theoretical studies reveal a reaction mechanism with nucleophilic addition followed by a swift proton transfer-induced elimination reaction. Nature Publishing Group UK 2021-10-13 /pmc/articles/PMC8514480/ /pubmed/34645807 http://dx.doi.org/10.1038/s41467-021-25836-5 Text en © The Author(s) 2021 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . |
spellingShingle | Article Guo, Yu Wang, Ruo-Ya Kang, Jia-Xin Ma, Yan-Na Xu, Cong-Qiao Li, Jun Chen, Xuenian Efficient synthesis of primary and secondary amides via reacting esters with alkali metal amidoboranes |
title | Efficient synthesis of primary and secondary amides via reacting esters with alkali metal amidoboranes |
title_full | Efficient synthesis of primary and secondary amides via reacting esters with alkali metal amidoboranes |
title_fullStr | Efficient synthesis of primary and secondary amides via reacting esters with alkali metal amidoboranes |
title_full_unstemmed | Efficient synthesis of primary and secondary amides via reacting esters with alkali metal amidoboranes |
title_short | Efficient synthesis of primary and secondary amides via reacting esters with alkali metal amidoboranes |
title_sort | efficient synthesis of primary and secondary amides via reacting esters with alkali metal amidoboranes |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8514480/ https://www.ncbi.nlm.nih.gov/pubmed/34645807 http://dx.doi.org/10.1038/s41467-021-25836-5 |
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