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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...

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Autores principales: Ren, Jing, Xu, Junhua, Kong, Xiangxiang, Li, Jinlong, Li, Kaizhi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
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.
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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
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