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

Changdong Shao; Tianyi Xu; Chen Chen; Qionglin Yang; Chao Tang; Ping Chen; Mingzhu Lu; Zhengsong Hu; Huayou Hu; Tingting Zhang

doi:10.1039/D3RA00088E

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

Changdong Shao,

*^a Tianyi Xu,^a Chen Chen,^a Qionglin Yang,^a Chao Tang,

^a Ping Chen,

^a Mingzhu Lu,

^a Zhengsong Hu,^a Huayou Hu

^a and Tingting Zhang*^a

Author affiliations

* Corresponding authors

^a Jiangsu Provincial Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an, Jiangsu, China
E-mail: shaochangdong@hytc.edu.cn

Abstract

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.

RSC Advances

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

Abstract

Supplementary files

Article information

Download Citation

Permissions

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

Social activity

Search articles by author

Spotlight

Advertisements