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Coordinating activation strategy enables 1,2-alkylamidation of alkynes
The radical 1,2-difunctionalization reaction of alkynes has been evolved into a versatile approach for expeditiously increasing the complexity of the common feedstock alkyne. However, intermolecular 1,2-carboamidation with general alkyl groups is an unsolved problem. Herein, we show that a coordinat...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10599465/ https://www.ncbi.nlm.nih.gov/pubmed/37886104 http://dx.doi.org/10.1039/d3sc03786j |
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author | Ren, Jing Xu, Junhua Kong, Xiangxiang Li, Jinlong Li, Kaizhi |
author_facet | Ren, Jing Xu, Junhua Kong, Xiangxiang Li, Jinlong Li, Kaizhi |
author_sort | Ren, Jing |
collection | PubMed |
description | The radical 1,2-difunctionalization reaction of alkynes has been evolved into a versatile approach for expeditiously increasing the complexity of the common feedstock alkyne. However, intermolecular 1,2-carboamidation with general alkyl groups is an unsolved problem. Herein, we show that a coordinating activation strategy could act as an efficient tool for enabling radical 1,2-alkylamidation of alkynes. With the employment of diacyl peroxides as both alkylating reagents and internal oxidants, a large library of β-alkylated enamides is constructed in a three-component manner from readily accessible amides and alkynes. This protocol exhibits broad substrate scope with good functional group compatibility and is amenable for late-stage functionalization of natural molecules and biologically compounds. |
format | Online Article Text |
id | pubmed-10599465 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-105994652023-10-26 Coordinating activation strategy enables 1,2-alkylamidation of alkynes Ren, Jing Xu, Junhua Kong, Xiangxiang Li, Jinlong Li, Kaizhi Chem Sci Chemistry The radical 1,2-difunctionalization reaction of alkynes has been evolved into a versatile approach for expeditiously increasing the complexity of the common feedstock alkyne. However, intermolecular 1,2-carboamidation with general alkyl groups is an unsolved problem. Herein, we show that a coordinating activation strategy could act as an efficient tool for enabling radical 1,2-alkylamidation of alkynes. With the employment of diacyl peroxides as both alkylating reagents and internal oxidants, a large library of β-alkylated enamides is constructed in a three-component manner from readily accessible amides and alkynes. This protocol exhibits broad substrate scope with good functional group compatibility and is amenable for late-stage functionalization of natural molecules and biologically compounds. The Royal Society of Chemistry 2023-09-30 /pmc/articles/PMC10599465/ /pubmed/37886104 http://dx.doi.org/10.1039/d3sc03786j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Ren, Jing Xu, Junhua Kong, Xiangxiang Li, Jinlong Li, Kaizhi Coordinating activation strategy enables 1,2-alkylamidation of alkynes |
title | Coordinating activation strategy enables 1,2-alkylamidation of alkynes |
title_full | Coordinating activation strategy enables 1,2-alkylamidation of alkynes |
title_fullStr | Coordinating activation strategy enables 1,2-alkylamidation of alkynes |
title_full_unstemmed | Coordinating activation strategy enables 1,2-alkylamidation of alkynes |
title_short | Coordinating activation strategy enables 1,2-alkylamidation of alkynes |
title_sort | coordinating activation strategy enables 1,2-alkylamidation of alkynes |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10599465/ https://www.ncbi.nlm.nih.gov/pubmed/37886104 http://dx.doi.org/10.1039/d3sc03786j |
work_keys_str_mv | AT renjing coordinatingactivationstrategyenables12alkylamidationofalkynes AT xujunhua coordinatingactivationstrategyenables12alkylamidationofalkynes AT kongxiangxiang coordinatingactivationstrategyenables12alkylamidationofalkynes AT lijinlong coordinatingactivationstrategyenables12alkylamidationofalkynes AT likaizhi coordinatingactivationstrategyenables12alkylamidationofalkynes |