Copper-catalyzed selective C5-H bromination and difluoromethylation of 8-aminoquinoline amides using ethyl bromodifluoroacetate as the bifunctional reagent

A simple and effective method for the copper-catalyzed selective C5-H bromination and difluoromethylation of 8-aminoquinoline amides with ethyl bromodifluoroacetate as the bifunctional reagent was developed. The combination of cupric catalyst and alkaline additive results in a C5-bromination reactio...

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Autores principales: Shao, Changdong, Xu, Tianyi, Chen, Chen, Yang, Qionglin, Tang, Chao, Chen, Ping, Lu, Mingzhu, Hu, Zhengsong, Hu, Huayou, Zhang, Tingting
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9977446/
https://www.ncbi.nlm.nih.gov/pubmed/36874938
http://dx.doi.org/10.1039/d3ra00088e
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author Shao, Changdong
Xu, Tianyi
Chen, Chen
Yang, Qionglin
Tang, Chao
Chen, Ping
Lu, Mingzhu
Hu, Zhengsong
Hu, Huayou
Zhang, Tingting
author_facet Shao, Changdong
Xu, Tianyi
Chen, Chen
Yang, Qionglin
Tang, Chao
Chen, Ping
Lu, Mingzhu
Hu, Zhengsong
Hu, Huayou
Zhang, Tingting
author_sort Shao, Changdong
collection PubMed
description A simple and effective method for the copper-catalyzed selective C5-H bromination and difluoromethylation of 8-aminoquinoline amides with ethyl bromodifluoroacetate as the bifunctional reagent was developed. The combination of cupric catalyst and alkaline additive results in a C5-bromination reaction, whereas cuprous catalyst combined with silver additive results in the C5-difluoromethylation reaction. This method has a broad substrate scope and allows for easy and convenient access to desired C5-functionalized quinolones with good to excellent yields.
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spelling pubmed-99774462023-03-02 Copper-catalyzed selective C5-H bromination and difluoromethylation of 8-aminoquinoline amides using ethyl bromodifluoroacetate as the bifunctional reagent Shao, Changdong Xu, Tianyi Chen, Chen Yang, Qionglin Tang, Chao Chen, Ping Lu, Mingzhu Hu, Zhengsong Hu, Huayou Zhang, Tingting RSC Adv Chemistry A simple and effective method for the copper-catalyzed selective C5-H bromination and difluoromethylation of 8-aminoquinoline amides with ethyl bromodifluoroacetate as the bifunctional reagent was developed. The combination of cupric catalyst and alkaline additive results in a C5-bromination reaction, whereas cuprous catalyst combined with silver additive results in the C5-difluoromethylation reaction. This method has a broad substrate scope and allows for easy and convenient access to desired C5-functionalized quinolones with good to excellent yields. The Royal Society of Chemistry 2023-03-01 /pmc/articles/PMC9977446/ /pubmed/36874938 http://dx.doi.org/10.1039/d3ra00088e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Shao, Changdong
Xu, Tianyi
Chen, Chen
Yang, Qionglin
Tang, Chao
Chen, Ping
Lu, Mingzhu
Hu, Zhengsong
Hu, Huayou
Zhang, Tingting
Copper-catalyzed selective C5-H bromination and difluoromethylation of 8-aminoquinoline amides using ethyl bromodifluoroacetate as the bifunctional reagent
title Copper-catalyzed selective C5-H bromination and difluoromethylation of 8-aminoquinoline amides using ethyl bromodifluoroacetate as the bifunctional reagent
title_full Copper-catalyzed selective C5-H bromination and difluoromethylation of 8-aminoquinoline amides using ethyl bromodifluoroacetate as the bifunctional reagent
title_fullStr Copper-catalyzed selective C5-H bromination and difluoromethylation of 8-aminoquinoline amides using ethyl bromodifluoroacetate as the bifunctional reagent
title_full_unstemmed Copper-catalyzed selective C5-H bromination and difluoromethylation of 8-aminoquinoline amides using ethyl bromodifluoroacetate as the bifunctional reagent
title_short Copper-catalyzed selective C5-H bromination and difluoromethylation of 8-aminoquinoline amides using ethyl bromodifluoroacetate as the bifunctional reagent
title_sort copper-catalyzed selective c5-h bromination and difluoromethylation of 8-aminoquinoline amides using ethyl bromodifluoroacetate as the bifunctional reagent
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9977446/
https://www.ncbi.nlm.nih.gov/pubmed/36874938
http://dx.doi.org/10.1039/d3ra00088e
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