Formal Reductive Amination of Carboxylic Acids via Iron-Catalyzed Photoredox Decarboxylative α-Aminomethylation

Here we report an iron-catalyzed photocatalytic protocol utilizing ligand-to-metal charge transfer (LMCT) for efficient decarboxylative reductive amination to synthesize tertiary alkylamines. The method employs readily available carboxylic acids and <i>N</i>,<i>O</i>-acetals under mild conditions (room temperature, 390 nm LED), achieving excellent yields (up to 89%) across diverse alkyl carboxylic acid substrates, including primary, secondary, and tertiary types (>40 examples). Furthermore, the protocol exhibits good tolerance toward sensitive functional groups and enables late-stage functionalization of pharmaceutical compounds, providing a practical synthetic tool for complex alkylamine construction.

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Publication Details

Journal
Organic Letters
Published
2025-11-13
DOI
https://doi.org/10.1021/acs.orglett.5c04273
Citations
4
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
3.74
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article

Formal Reductive Amination of Carboxylic Acids via Iron-Catalyzed Photoredox Decarboxylative α-Aminomethylation

Donghui Xing, Jianmin Huang, Liangbin Huang, Xiaohong Li
4 citations
Organic Letters
Radical Photochemical Reactions
3.74
article

Formal Reductive Amination of Carboxylic Acids via Iron-Catalyzed Photoredox Decarboxylative α-Aminomethylation

Donghui Xing, Jianmin Huang, Liangbin Huang, Xiaohong Li
article en
4 citations

Abstract

Here we report an iron-catalyzed photocatalytic protocol utilizing ligand-to-metal charge transfer (LMCT) for efficient decarboxylative reductive amination to synthesize tertiary alkylamines. The method employs readily available carboxylic acids and <i>N</i>,<i>O</i>-acetals under mild conditions (room temperature, 390 nm LED), achieving excellent yields (up to 89%) across diverse alkyl carboxylic acid substrates, including primary, secondary, and tertiary types (>40 examples). Furthermore, the protocol exhibits good tolerance toward sensitive functional groups and enables late-stage functionalization of pharmaceutical compounds, providing a practical synthetic tool for complex alkylamine construction.

Organic LettersVol. 27(47)
Key Laboratory of Guangdong Province (CN), State Key Laboratory of Pulp and Paper Engineering, South China University of Technology (CN)
Openalex Percentile: Top 7%
Radical Photochemical Reactions
3.74
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