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Published on: August 12, 2019
Formal Reductive Amination of Carboxylic Acids via Iron-Catalyzed Photoredox Decarboxylative α-Aminomethylation
Jinxi Huang1, Donghui Xing1, Xiaohong Li1
1State Key Laboratory of Pulp and Paper Engineering, Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641, China.
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 N,O-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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