Practical chemoselective aromatic substitution: the synthesis of N -(4-halo-2-nitrophenyl)benzenesulfonamide through the efficient nitration and halogenation of N -phenylbenzenesulfonamide

A novel route involving the metal-promoted tandem nitration and halogenation of -phenylbenzenesulfonamide to synthesize -(4-halo-2-nitrophenyl)benzenesulfonamide derivatives has been developed. The method shows highly practical chemoselective and functional group compatibility. In addition, it emplo...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-07, Vol.20 (27), p.5444-5451
Main Authors: Yu, Xiao, Zhu, Wenjing, Liu, Hongyan, Liu, Yi, Li, Hongshuang, Han, Junfen, Duan, Guiyun, Bai, Zhushuang, Zhang, Pengfei, Xia, Chengcai
Format: Article
Language:English
Subjects:
Ammonium nitrate
Benzenesulfonamides
Benzimidazoles
Copper
Functional groups
Halogenation
Molecular Structure
Nitration
Quinoxaline
Quinoxalines
Reagents
Sulfonamides
Synthesis
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Summary:A novel route involving the metal-promoted tandem nitration and halogenation of -phenylbenzenesulfonamide to synthesize -(4-halo-2-nitrophenyl)benzenesulfonamide derivatives has been developed. The method shows highly practical chemoselective and functional group compatibility. In addition, it employs insensitive and inexpensive Cu(NO ) ·3H O, Fe(NO ) ·9H O, and NH NO as the nitration reagents, and it provides a direct approach for the preparation of 4-halo-2-nitroaniline, which is a crucial intermediate for the synthesis of benzimidazoles and quinoxaline derivatives.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob01028c