Visible-Light-Promoted Ceric Ammonium Nitrate Catalysis Enables the Intramolecular Dehydrogenative Lactonization of Aromatic Carboxylic Acids

doi:10.6023/cjoc202602014

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (10): 4141-4151.DOI: 10.6023/cjoc202602014 Previous Articles Next Articles

ARTICLES

可见光促进硝酸铈铵催化芳香羧酸的分子内脱氢酯化

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精细化工过程替代技术浙江省重点实验室浙江绍兴 312000
^b 绍兴大学浙江省脂溶性维生素工程技术研究中心浙江省脂溶性维生素工程技术研究中心浙江绍兴 312000

收稿日期:2026-02-13 修回日期:2026-04-12 发布日期:2026-06-03
通讯作者: 冯高峰, 余乐茂
基金资助:
国家自然科学基金(21672166); 国家自然科学基金(21302130)

Visible-Light-Promoted Ceric Ammonium Nitrate Catalysis Enables the Intramolecular Dehydrogenative Lactonization of Aromatic Carboxylic Acids

Gaofeng Feng^a^,^*(), Yisha Wang^a, Xuhong Wang^a, Pengyu Wang^a, Cheng'an Jin^a, Hang Jiang^a, Xingcheng Ding^a, Tao Cai^b, Lemao Yu^a^,^*()

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

Received:2026-02-13 Revised:2026-04-12 Published:2026-06-03
Contact: Gaofeng Feng, Lemao Yu
Supported by:
National Natural Science Foundation of China(21672166); National Natural Science Foundation of China(21302130)

1. .pdf(17107KB)

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/dehaloge-nation 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, ceric ammonium nitrate (CAN) catalysis, lactonization, benzo-3,4-coumarin derivatives

Cite this article

Gaofeng Feng, Yisha Wang, Xuhong Wang, Pengyu Wang, Cheng'an Jin, Hang Jiang, Xingcheng Ding, Tao Cai, Lemao Yu. Visible-Light-Promoted Ceric Ammonium Nitrate Catalysis Enables the Intramolecular Dehydrogenative Lactonization of Aromatic Carboxylic Acids[J]. Chinese Journal of Organic Chemistry, 2026, 46(10): 4141-4151.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

References 30

[1]	For representative reviews: (a) Prier C. K.; Rankic D. A.; Macmillan D. W. C. Chem. Rev. 2013, 113, 5322. doi: 10.1021/cr300503r
	(b) Schultz D. M.; Yoon T. P. Science 2014, 343, 1239176. doi: 10.1126/science.1239176
	(c) Shaw M. H.; Twilton J.; Macmillan D. W. C. J. Org. Chem. 2016, 81, 6898. doi: 10.1021/acs.joc.6b01449
[2]	For selected examples: (a) King K. A.; Spellane P. JQ.; Watts R. J. J. Am. Chem. Soc. 1985, 107, 1431. doi: 10.1021/ja00291a064 pmid: 26316601
	(b) Musacchio A. J.; Nguyen L. Q.; Beard G. H.; Knowles R. R. J. Am. Chem. Soc. 2014, 136, 12217. doi: 10.1021/ja5056774 pmid: 26316601
	(c) Jeffrey J. L.; Terrett J. A.; MacMillan D. W. C. Science 2015, 349, 1532. doi: 10.1126/science.aac8555 pmid: 26316601
	(d) Cuthbertson J. D.; MacMillan D. W. C. Nature 2015, 519, 74. doi: 10.1038/nature14255 pmid: 26316601
	(e) Choi G. J.; Zhu Q.; Miller D. C.; Gu C. J.; Knowles R. R. Nature 2016, 539, 268. doi: 10.1038/nature19811 pmid: 26316601
	(f) Chu J. C. K.; Rovis T. Nature 2016, 539, 272. doi: 10.1038/nature19810 pmid: 26316601
	(g) Hu X.; Chen J.; Xiao W. Angew. Chem.,Int. Ed. 2017, 56, 1960. doi: 10.1002/anie.v56.8 pmid: 26316601
[3]	(a) Abderrazak Y.; Bhattacharyya A.; Reiser O. Angew. Chem.,Int. Ed. 2021, 60, 21100. doi: 10.1002/anie.v60.39
	(b) Birnthaler D.; Narobe R.; Lopez-Berguno E.; Haag C.; König B. ACS Catal. 2023, 13, 1125. doi: 10.1021/acscatal.2c05631
	(c) An Q.; Chang L.; Zuo Z. W. Acc. Chem. Res. 2024, 57, 2915. doi: 10.1021/acs.accounts.4c00510
[4]	(a) Tsurugi H.; Mashima K. J. Am. Chem. Soc. 2021, 143, 7879. doi: 10.1021/jacs.1c02889
	(b) Chang L.; An Q.; Duan L.; Feng K.; Zuo Z. Chem. Rev. 2022, 122, 2429. doi: 10.1021/acs.chemrev.1c00256
	(c) An Q.; Xing Y. Y.; Pu R.; Jia M.; Chen Y.; Hu A.; Zhang S. Q.; Yu N.; Du J.; Zhang Y.; Chen J.; Liu W.; Hong X.; Zuo Z. J. Am. Chem. Soc. 2023, 145, 359. doi: 10.1021/jacs.2c10126
[5]	(a) Tsui E.; Wang H.; Knowles R. R. Chem. Sci. 2020, 11, 11124. doi: 10.1039/D0SC04542J
	(b) Chang L.; Wang S.; An Q.; Liu L.; Wang H.; Li Y.; Feng K.; Zuo Z. Chem. Sci. 2023, 14, 6841. doi: 10.1039/D3SC01118F
[6]	(a) Guo J. J.; Hu A.; Chen Y.; Sun J.; Tang H.; Zuo Z. Angew. Chem. Int. Ed. 2016, 55, 15319. doi: 10.1002/anie.v55.49
	(b) Müller N.; Stahl J.; Stoiber J.; König B. Eur. J. Org. Chem. 2025, 28. e202500373.
[7]	(a) Hu A. H.; Guo J. J.; Pan H; Zuo Z. W. Science 2018, 361, 668. doi: 10.1126/science.aat9750
	(b) Hu A.; Guo J. J.; Pan H.; Tang H.; Gao Z.; Zuo Z. J. Am. Chem. Soc. 2018, 140, 1612. doi: 10.1021/jacs.7b13131
	(c) Schwarz J.; Konig B. Chem. Commun. 2019, 55, 486. doi: 10.1039/C8CC09208G
[8]	(a) Zhang K.; Chang L.; An Q.; Wang X.; Zuo Z. J. Am. Chem. Soc. 2019, 141, 10556. doi: 10.1021/jacs.9b05932
	(b) Chen Y.; Wang X.; He X.; An Q.; Zuo Z. J. Am. Chem. Soc. 2021, 143, 4896. doi: 10.1021/jacs.1c00618
[9]	Shirase S.; Tamaki S.; Shinohara K.; Hirosawa K.; Tsurugi H.; Satoh T.; Mashima K. J. Am. Chem. Soc. 2020, 142, 5668. doi: 10.1021/jacs.9b12918
[10]	Li P.; Duan L.; Lin Y.; Chu L.; Zuo Z. Angew. Chem. Int. Ed. 2025, 64, e202501949.
[11]	Zhu X. L.; Chen Y. F.; Zhou L. N. Org. Lett. 2025, 27, 13419. doi: 10.1021/acs.orglett.5c03951
[12]	For selected examples of carboxylic acids as HAT agents: (a) Shan Y.; Gao F. Q.; Xu C.; Liu H. W.; Tang L.; Zhang J. J.; Wang W.; Chen Z.; Chen Z. Org. Lett. 2025, 27, 12223. doi: 10.1021/acs.orglett.5c03502
	(b) Qian P.; Zhu D.; Wang X.; Sun Q.; Zhang S. J. Org. Chem. 2024, 89, 6395. doi: 10.1021/acs.joc.4c00425
	(c) Hirose M.; Sakaguchi H.; Hashimoto R.; Furutani T.; Yamawaki M.; Suzuki H.; Yoshimi Y. Chemistry 2024, 30, e202402285.
	(d) Li H.; Qiao K.; Jiang W.; Li F.; Shi L. Chem. Commun. 2024, 60, 9416. doi: 10.1039/D4CC02792B
[13]	For selected examples of decarboxylation reactions: (a) Li Z.; Wang X.; Xia S.; Jin J. Org. Lett. 2019, 21, 4259. doi: 10.1021/acs.orglett.9b01439
	(b) Feng G.; Wang X.; Jin J. Eur. J. Org. Chem. 2019, 2019, 6728. doi: 10.1002/ejoc.v2019.39
	(c) Chen T. Q.; Pedersen P. S.; Dow N. W.; Fayad R.; Hauke C. E.; Rosko M. C.; Danilov E. O.; Blakemore D. C.; Dechert-Schmitt A. M.; Knauber T.; Castellano F. N.; MacMillan D. W. C. J. Am. Chem. Soc. 2022, 144, 8296. doi: 10.1021/jacs.2c02392
[14]	(a) Ramirez N. P.; Bosque I.; Gonzalez-Gomez J. C. Org. Lett. 2015, 17, 4550. doi: 10.1021/acs.orglett.5b02269 pmid: 26323040
	(b) Yang Q.; Jia Z.; Li L.; Zhang L.; Luo S. Org. Chem. Front. 2018, 5, 237. doi: 10.1039/C7QO00826K pmid: 26323040
[15]	Morack T.; Metternich J. B.; Gilmour R. Org. Lett. 2018, 20, 1316. doi: 10.1021/acs.orglett.8b00052
[16]	Shi G.; Wang Y.; He M.; Yu X.; Bao M. Org. Chem. Front. 2023, 10, 2429. doi: 10.1039/D3QO00368J
[17]	Sen P. P.; Pathania V.; Raha Roy S. Org. Chem. Front. 2024, 11, 106. doi: 10.1039/D3QO01662E
[18]	Xia S.; Hu K.; Lei C.; Jin J. Org. Lett. 2020, 22, 1385. doi: 10.1021/acs.orglett.0c00002
[19]	Sen P. P.; Raha Roy S. Organometallics 2023, 42, 1658. doi: 10.1021/acs.organomet.3c00210
[20]	Wadekar K.; Aswale S.; Yatham V. R. Org. Biomol. Chem. 2020, 18, 983. doi: 10.1039/c9ob02676b pmid: 31939464
[21]	Chao M.; Wang F.; Xu L.; Ju Y.; Chen Z.; Wang B.; Gong P.; You J.; Jin M.; Shen D. J. Org. Chem. 2021, 86, 13371. doi: 10.1021/acs.joc.1c01479
[22]	Feng G.; Zhang C.; He J. Y.; Cai T.; Xu W.; Jin J. Org. Lett. 2025, 27, 3501. doi: 10.1021/acs.orglett.5c00108
[23]	Wei C.; Chang D.; Feng N.; Zhan Z.; Shi L. Org. Lett. 2025, 27, 2582. doi: 10.1021/acs.orglett.5c00185
[24]	Zhu C.; Zhang Y.; Kan J.; Zhao H.; Su W. Org. Lett. 2015, 17, 3418. doi: 10.1021/acs.orglett.5b01398
[25]	Li Y.; Ding Y. J.; Wang J. Y.; Su Y. M.; Wang X. S. Org. Lett. 2013, 15, 2574. doi: 10.1021/ol400877q
[26]	Gao P.; Wei Y. Synthesis 2013, 46, 343. doi: 10.1055/s-00000084
[27]	Pan C.; Wang L.; Han J. Org. Lett. 2020, 22, 4776. doi: 10.1021/acs.orglett.0c01577
[28]	Zhang Y.; Tian Y.; Xiang P.; Huang N.; Wang J.; Xu J. H.; Zhang M. Org. Biomol. Chem. 2016, 14, 9874. pmid: 27722745
[29]	Zhang L.; Zhang Z.; Hong J.; Yu J.; Zhang J.; Mo F. J. Org. Chem. 2018, 83, 3200. doi: 10.1021/acs.joc.8b00089
[30]	Li J.; Chen H.; Zhang-Negrerie D.; Du Y.; Zhao K. RSC Adv. 2013, 3, 4311. doi: 10.1039/c3ra23188g

Entry	Variations from the standard conditions	Yield^b/%
1	None	82
2	O₂ balloon instead of NaBrO₃	35
3	Na₂S₂O₄; NaIO₄; (NH₄)₂S₂O₈ instead of NaBrO₃	39; 35; 31
4	HFIP; toluene; CH₂Cl₂/H₂O (V/V=1∶1) instead of MeCN	67; 0; 20
5	390 nm Kessil lamp	81
6	440 nm Kessil lamp	80
7	No CAN	20
8	No CAN and no NaBrO₃	10
9	No light	n.r.
10	Under N₂ atmosphere	91
11	90 ℃ bath instead of Kessil lamp	35

Entry	Variations from the standard conditions	Yield^b/%
1	None	82
2	O₂ balloon instead of NaBrO₃	35
3	Na₂S₂O₄; NaIO₄; (NH₄)₂S₂O₈ instead of NaBrO₃	39; 35; 31
4	HFIP; toluene; CH₂Cl₂/H₂O (V/V=1∶1) instead of MeCN	67; 0; 20
5	390 nm Kessil lamp	81
6	440 nm Kessil lamp	80
7	No CAN	20
8	No CAN and no NaBrO₃	10
9	No light	n.r.
10	Under N₂ atmosphere	91
11	90 ℃ bath instead of Kessil lamp	35

可见光促进硝酸铈铵催化芳香羧酸的分子内脱氢酯化

Visible-Light-Promoted Ceric Ammonium Nitrate Catalysis Enables the Intramolecular Dehydrogenative Lactonization of Aromatic Carboxylic Acids

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 6

References 30

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Bin Huang, Zhantu Xu, Jing Chen, Weiping Su, Chen Zhu. Advances in Visible-Light Induced Trifluoromethylation with Trifluoroacetic Acid and Its Anhydride as Inexpensive and Effective Trifluoromethylation Reagents [J]. Chinese Journal of Organic Chemistry, 2026, 46(9): 3461-3479.
[2]	Xiao-Jun He, Bin Chen, Xiao-Ning Guo, Chen-Ho Tung, Li-Zhu Wu. Photocatalytic C(sp²)—C(sp³) Cross-Coupling between C(sp²)—Cl Bond and C(sp³)—H Bond [J]. Chinese Journal of Organic Chemistry, 2026, 46(9): 3640-3645.
[3]	Yixuan Chen, Zheng Zhao. Aggregation-Induced Emission Photocatalysts for Fast and Oxygen-Tolerant Radical Photopolymerization [J]. Chinese Journal of Organic Chemistry, 2026, 46(9): 3587-3593.
[4]	Rui Wu, Zhiquan Wu, Juan Zhang, Wenchao Gao, Yingxiong Wang, Honghong Chang. Research Progress in the Selective Catalytic Oxidation of Ethylene Glycol to Glycolic Acid [J]. Chinese Journal of Organic Chemistry, 2026, 46(8): 2969-2987.
[5]	Lizhuo Wang, Xinyi Liu, Geyang Song, Xiaoli Shi, Dong Xue. Photoexcitation-Enabled C(sp²)—N Coupling of Aryl Halides with Sulfonamides Catalyzed by Earth-Abundant Nickel [J]. Chinese Journal of Organic Chemistry, 2026, 46(7): 2835-2852.
[6]	An Chen, Zeyi Wang, Wanmei Li, Jun Xu. Recent Advances in the Light-Driven One-Step Synthesis of Dual Carbon-Substituted Bicyclo[1.1.1]pentanes [J]. Chinese Journal of Organic Chemistry, 2026, 46(6): 2177-2192.
[7]	Ying Xu, Meilin Yang, Dapeng Cui, Miao Yu, Yingjie Liu. Research Progress on Defluorination Reactions [J]. Chinese Journal of Organic Chemistry, 2026, 46(5): 1962-1983.
[8]	Ziming Zhao, Jianfeng Zheng, Peiqiang Huang. Progress on the Photocatalytic Synthesis of Amines from Imines [J]. Chinese Journal of Organic Chemistry, 2026, 46(5): 1984-2001.
[9]	Xi Cheng, Yalin Li, Peng Wu, Min Su, Zixuan Zhang, Minjun Jiao, Xuefen Liu, Shuping Luo. Anthraquinone-Based Photosensitizers: Design, Synthesis and Application in Photocatalytic C(sp³)—H Oxidation [J]. Chinese Journal of Organic Chemistry, 2026, 46(5): 2104-2111.
[10]	Xinyi Hou, Tongtong Shi, Zejiang Li, Qinghao Dong, Kai Sun, Xin Wang. Visible-Light-Induced Phosphorylation Cyclization to Phosphorylated Indole-Fused Diazepines [J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1776-1787.
[11]	Jingfei Zheng, Qiyan Lv, Kai Sun, Xiaolan Chen, Lingbo Qu, Jinquan Wang, Bing Yu. Recent Advances in Functionalization of 6-Azauracils via Radical Reactions [J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1603-1620.
[12]	Yuqing Zhao, Xianjin Zhu, Lingyu Shi, Mingyu Wei, Zihan Xu, Yongjia Shi, Xufeng Li, Daoshan Yang. Research Progress on the Ring-Opening Functionalization of Cyclic Sulfonium Salts [J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1572-1602.
[13]	Shan Yang, Yasu Chen, Chen Zhu. Construction of N-Fused Heteroarenes via Radical-Mediated Functional Group Migration-Cyclization [J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1739-1749.
[14]	Linyu Lu, Yutong Qi, Tinghui Zhang, Shengnan Jin, Zhongyan Cao, Hongwei Zhang. Recent Progress in Radical Mediated 1,2,n-Trifunctiona-lization of Olefins [J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1540-1559.
[15]	Jianyang Dong, Dong Xue. Research Progress on the Functionalization of [1.1.1]Propellane via Radical Pathways [J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1464-1480.