期刊
ACS CATALYSIS
卷 12, 期 21, 页码 13225-13233出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c04417
关键词
heterocycles; photocatalysis; carboxylic acid; amidyl radical; C-H functionalization
资金
- Institute for Basic Science
- [IBS -R010 -A2]
A highly efficient visible-light-mediated C-H alkylation of pyridines at the C4 position using alkyl carboxylic acids as alkylating agents is reported in this study. The released N-centered radical acts as an effective oxidizing agent for single-electron transfer (SET) oxidation to regenerate the photocatalyst, making this photocatalytic system appealing from a mechanistic perspective. The strategy offers a practical approach for the C4-selective pyridylation of carboxylic acids and amino acids with various functional groups under mild, metal-free conditions.
Site-selective C-H functionalization of heteroarenes is important for the rapid modification of bioactive molecules. Herein, we report an efficient photocatalytic platform for the visible-light-mediated C-H alkylation of pyridines at the C4 position using alkyl carboxylic acids as alkylating agents under external oxidant-free conditions. Importantly, the released N-centered radical can serve as an effective oxidizing agent for single-electron transfer (SET) oxidation to efficiently regenerate the photocatalyst. This photocatalytic system is appealing from a mechanistic perspective and is amenable to a broad substrate scope for carboxylic acids and pyridines containing oxidatively sensitive functionalities that do not hold up to other procedures. The strategy offers a practical approach for the C4-selective pyridylation of a diverse range of primary, secondary, and tertiary carboxylic acids and amino acids with various functional groups under mild, metal-free conditions.
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