Visible-Light-Promoted CAN Catalysis Enables Intramolecular Dehydrogenative Lactonization of Aromatic Carboxylic Acids

doi:10.6023/cjoc202602014

Chinese Journal of Organic Chemistry

ARTICLE

可见光促进硝酸铈铵催化芳香羧酸分子内脱氢酯化

冯高峰^a,*, 王怡莎^a, 王旭宏^a, 王鹏宇^a, 金成安^a, 蒋航^a, 丁兴成^a, 蔡涛^b, 余乐茂^a,*

^a绍兴大学上虞分院,精细化工过程替代技术浙江省重点实验室,绍兴 312000;
^b绍兴大学浙江省脂溶性维生素工程技术研究中心,绍兴 312000

收稿日期:2026-02-13 修回日期:2026-04-12
基金资助:
国家自然科学基金(No. 21672166 and 21302130 )资助项目.

Visible-Light-Promoted CAN Catalysis Enables Intramolecular Dehydrogenative Lactonization of Aromatic Carboxylic Acids

Gaofeng Feng^a,*, Yisha Wang^a, Xu-Hong Wang^a, Peng-Yu Wang^a, Chengan Jin^a, Hang Jiang^a, Xingcheng Ding^a, Tao Cai^b, Lemao Yu^a,*

^a Shangyu College and Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. China;
^b Zhejiang Engineering Research Center of Fat-Soluble Vitamin, Shaoxing University, Shaoxing 312000, P.R. China

Received:2026-02-13 Revised:2026-04-12
Contact: ^*E-mail: chfeng@usx.edu.cn; yulm@usx.edu.cn
Supported by:
National Natural Science Foundation of China (No. 21672166 and 21302130).

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Abstract

A visible-light-mediated ceric ammonium nitrate (CAN) catalyzed protocol for intramolecular lactonization of aromatic carboxylic acids, involving a sequence of acyloxy radical generation via ligand-to-metal charge-transfer (LMCT) of aryl carboxylate-Ce(IV) complex under visible light irradiation, intramolecular cyclization, and dehydrogenation/dehalogenation of C(sp²)-H or C(sp²)-X (X = F, Cl, Br) bond, has been developed. A wide range of functional groups could be readily tolerated under this newly developed protocol, and 37 examples of valuable benzo-3,4-coumarin and 4-substituted coumarin derivatives have been conveniently synthesized in good to excellent yields. The protocol features simple operation, employment of cheap and readily available reagents, thus possesses potential practical applications.

Key words: photocatalysis, CAN catalysis, lactonization, benzo-3,4-coumarin derivatives

Cite this article

Gaofeng Feng, Yisha Wang, Xu-Hong Wang, Peng-Yu Wang, Chengan Jin, Hang Jiang, Xingcheng Ding, Tao Cai, Lemao Yu. Visible-Light-Promoted CAN Catalysis Enables Intramolecular Dehydrogenative Lactonization of Aromatic Carboxylic Acids[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202602014.

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可见光促进硝酸铈铵催化芳香羧酸分子内脱氢酯化

Visible-Light-Promoted CAN Catalysis Enables Intramolecular Dehydrogenative Lactonization of Aromatic Carboxylic Acids

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