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Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines
Alkyl carboxylic acids as well as primary amines are ubiquitous in all facets of biological science, pharmaceutical science, chemical science and materials science. By chemical conversion to redox-active esters (RAE) and Katritzky’s N-alkylpyridinium salts, respectively, alkyl carboxylic acids and p...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7542462/ https://www.ncbi.nlm.nih.gov/pubmed/33028818 http://dx.doi.org/10.1038/s41467-020-18834-6 |
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author | Li, Zhan Wang, Ke-Feng Zhao, Xin Ti, Huihui Liu, Xu-Ge Wang, Honggen |
author_facet | Li, Zhan Wang, Ke-Feng Zhao, Xin Ti, Huihui Liu, Xu-Ge Wang, Honggen |
author_sort | Li, Zhan |
collection | PubMed |
description | Alkyl carboxylic acids as well as primary amines are ubiquitous in all facets of biological science, pharmaceutical science, chemical science and materials science. By chemical conversion to redox-active esters (RAE) and Katritzky’s N-alkylpyridinium salts, respectively, alkyl carboxylic acids and primary amines serve as ideal starting materials to forge new connections. In this work, a Mn-mediated reductive decarboxylative/deaminative functionalization of activated aliphatic acids and primary amines is disclosed. A series of C-X (X = S, Se, Te, H, P) and C-C bonds are efficiently constructed under simple and mild reaction conditions. The protocol is applicable to the late-stage modification of some structurally complex natural products or drugs. Preliminary mechanistic studies suggest the involvement of radicals in the reaction pathway. |
format | Online Article Text |
id | pubmed-7542462 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-75424622020-10-19 Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines Li, Zhan Wang, Ke-Feng Zhao, Xin Ti, Huihui Liu, Xu-Ge Wang, Honggen Nat Commun Article Alkyl carboxylic acids as well as primary amines are ubiquitous in all facets of biological science, pharmaceutical science, chemical science and materials science. By chemical conversion to redox-active esters (RAE) and Katritzky’s N-alkylpyridinium salts, respectively, alkyl carboxylic acids and primary amines serve as ideal starting materials to forge new connections. In this work, a Mn-mediated reductive decarboxylative/deaminative functionalization of activated aliphatic acids and primary amines is disclosed. A series of C-X (X = S, Se, Te, H, P) and C-C bonds are efficiently constructed under simple and mild reaction conditions. The protocol is applicable to the late-stage modification of some structurally complex natural products or drugs. Preliminary mechanistic studies suggest the involvement of radicals in the reaction pathway. Nature Publishing Group UK 2020-10-07 /pmc/articles/PMC7542462/ /pubmed/33028818 http://dx.doi.org/10.1038/s41467-020-18834-6 Text en © The Author(s) 2020 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/. |
spellingShingle | Article Li, Zhan Wang, Ke-Feng Zhao, Xin Ti, Huihui Liu, Xu-Ge Wang, Honggen Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines |
title | Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines |
title_full | Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines |
title_fullStr | Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines |
title_full_unstemmed | Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines |
title_short | Manganese-mediated reductive functionalization of activated aliphatic acids and primary amines |
title_sort | manganese-mediated reductive functionalization of activated aliphatic acids and primary amines |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7542462/ https://www.ncbi.nlm.nih.gov/pubmed/33028818 http://dx.doi.org/10.1038/s41467-020-18834-6 |
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