Direct Photocatalytic Reductive Amidation of Nitroarenes: A Tandem Reduction–Decarboxylation Approach to Amide Bond Construction

We report a photocatalytic strategy for direct amide synthesis from readily available nitroarenes and benzoylformic acids using flavin as an efficient photocatalyst. This one-pot transformation proceeds through a tandem reduction-decarboxylation-amidation sequence under mild blue light irradiation. Preliminary mechanistic studies indicated that nitrosoarene and <i>N</i>-hydroxyamides could be the key intermediates. The method demonstrates a broad substrate scope, excellent functional group tolerance, and remarkable operational simplicity, as it can be conducted under an ambient atmosphere. Notably, this protocol represents a significant advancement in step economy by directly employing diverse nitroarenes as nitrogen sources, avoiding the need for pre-reduced amine intermediates.

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Publication Details

Journal
Organic Letters
Published
2025-05-15
DOI
https://doi.org/10.1021/acs.orglett.5c01371
Citations
6
Primary Topic
Chemical Synthesis and Analysis
Type
article
Field-Weighted Citation Impact
4.84

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article

Direct Photocatalytic Reductive Amidation of Nitroarenes: A Tandem Reduction–Decarboxylation Approach to Amide Bond Construction

Chenwei Liu, Xiaowen Qin, Shuhui Sun, Zhiping Yin et al.
6 citations
Organic Letters
Chemical Synthesis and Analysis
4.84
article

Direct Photocatalytic Reductive Amidation of Nitroarenes: A Tandem Reduction–Decarboxylation Approach to Amide Bond Construction

Chenwei Liu, Xiaowen Qin, Shuhui Sun, Zhiping Yin, Heng Li, Hongxia Li, Weiheng Yuan, Tiefeng Xu
article en
6 citations

Abstract

We report a photocatalytic strategy for direct amide synthesis from readily available nitroarenes and benzoylformic acids using flavin as an efficient photocatalyst. This one-pot transformation proceeds through a tandem reduction-decarboxylation-amidation sequence under mild blue light irradiation. Preliminary mechanistic studies indicated that nitrosoarene and <i>N</i>-hydroxyamides could be the key intermediates. The method demonstrates a broad substrate scope, excellent functional group tolerance, and remarkable operational simplicity, as it can be conducted under an ambient atmosphere. Notably, this protocol represents a significant advancement in step economy by directly employing diverse nitroarenes as nitrogen sources, avoiding the need for pre-reduced amine intermediates.

Organic LettersVol. 27(21)
Jiangsu University (CN), Zhejiang Sci-Tech University (CN)
China Postdoctoral Science Foundation, Senior Talent Foundation of Jiangsu University, Natural Science Research of Jiangsu Higher Education Institutions of China, Graduate Research and Innovation Projects of Jiangsu Province
Openalex Percentile: Top 5%
Chemical Synthesis and Analysis
4.84
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