Light‐Promoted Synthesis of Arylamines from Nitro Compounds and Grignard Reagents

Comprehensive Summary Arylamines constitute a fundamental class of organic compounds critical to pharmaceuticals, dyes, and advanced materials. The direct synthesis of arylamines from nitro compounds demonstrates significant advantages in step economy, cost efficiency, and functional group compatibility. However, conventional methodologies frequently necessitate transition metal catalysts or excessive reducing agents, limiting their practical applicability. Herein, we introduce a highly efficient photochemical protocol for the synthesis of arylamines from readily accessible nitro compounds and Grignard reagents under purple light (390—395 nm) irradiation, eliminating the requirement for transition metal catalysts or external reducing agents. This protocol exhibits exceptional tolerance to sterically hindered substrates and sensitive functional groups. Preliminary mechanistic investigations suggest the involvement of nitrosoarenes and diarylamine nitrogen radicals as key intermediates in the reaction pathway.

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Publication Details

Journal
Chinese Journal of Chemistry
Published
2025-04-18
DOI
https://doi.org/10.1002/cjoc.70029
Citations
2
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
Field-Weighted Citation Impact
1.87

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article

Light‐Promoted Synthesis of Arylamines from Nitro Compounds and Grignard Reagents

Tengfei Kang, Zhang‐Jie Shi, Yang Chen, Gang Li et al.
2 citations
Chinese Journal of Chemistry
Catalytic Cross-Coupling Reactions
1.87
article

Light‐Promoted Synthesis of Arylamines from Nitro Compounds and Grignard Reagents

Tengfei Kang, Zhang‐Jie Shi, Yang Chen, Gang Li, Dong Xue, Yu Wan, Tong Sun
article en
2 citations

Abstract

Comprehensive Summary Arylamines constitute a fundamental class of organic compounds critical to pharmaceuticals, dyes, and advanced materials. The direct synthesis of arylamines from nitro compounds demonstrates significant advantages in step economy, cost efficiency, and functional group compatibility. However, conventional methodologies frequently necessitate transition metal catalysts or excessive reducing agents, limiting their practical applicability. Herein, we introduce a highly efficient photochemical protocol for the synthesis of arylamines from readily accessible nitro compounds and Grignard reagents under purple light (390—395 nm) irradiation, eliminating the requirement for transition metal catalysts or external reducing agents. This protocol exhibits exceptional tolerance to sterically hindered substrates and sensitive functional groups. Preliminary mechanistic investigations suggest the involvement of nitrosoarenes and diarylamine nitrogen radicals as key intermediates in the reaction pathway.

Chinese Journal of ChemistryVol. 43(14)
Fudan University (CN), Shaanxi Normal University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Shaanxi Province, Fundamental Research Funds for the Central Universities
Openalex Percentile: Top 15%
Catalytic Cross-Coupling Reactions
1.87
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