Visible-Light-Triggered Self-Catalyzed Tandem Difluoromethylation/Cyclization of 2-Isocyanobiphenyls with Alkyl Bromodifluoroacetates

doi:10.6023/A26070262

Acta Chimica Sinica ›› 2026, Vol. 84 ›› Issue (9): 1399-1404.DOI: 10.6023/A26070262 Previous Articles Next Articles

Communication

可见光触发2-异氰基联苯与二氟溴乙酸酯自催化二氟甲基化/环化串联反应

彭佳^a^,^†, 杨云^a^,^†, 蔡迎丽^a, 易荣楠^b^,^*(), 姜东方^c, 唐裕才^d^,^e, 吴超^a^,^*(), 叶龙武^a^,^*(), 何卫民^a^,^*()

^a 南华大学化学化工学院湖南衡阳 421001
^b 湖南警察学院食药环及毒品检验技术湖南省普通高等学校重点实验室食药环及毒品检验技术湖南省普通高等学校重点实验室长沙 410138
^c 长沙医学院功能核酸基础与临床湖南省普通高校重点实验室功能核酸基础与临床湖南省普通高校重点实验室长沙 410219
^d 湖南文理学院化学与材料工程学院湖南常德 415000
^e 南京林业大学化学工程学院南京 210037

投稿日期:2026-07-23 发布日期:2026-08-17
通讯作者: 易荣楠, 吴超, 叶龙武, 何卫民
作者简介:
^† 共同第一作者
基金资助:
湖南省自然科学基金(2026JJ90135); 湖南省科技创新计划(2023RC4004); 湖南省教育厅科学研究项目(25A0703); 湖南省教育厅科学研究项目(23B0411); 长沙市自然科学基金(104872)

Visible-Light-Triggered Self-Catalyzed Tandem Difluoromethylation/Cyclization of 2-Isocyanobiphenyls with Alkyl Bromodifluoroacetates

Jia Peng^a, Yun Yang^a, Yingli Cai^a, Rongnan Yi^b^,^*(), Dongfang Jiang^c, Yucai Tang^d^,^e, Chao Wu^a^,^*(), Longwu Ye^a^,^*(), Weimin He^a^,^*()

^a School of Chemistry and Chemical Engineering, University of South China, Hengyang, Hunan 421001, China
^b Key Laboratory of Food & Environment & Drug Monitoring and Testing of Universities in Hunan Province, Hunan Police Academy, Changsha 410138, China
^c Hunan Provincial University Key Laboratory of the Fundamental and Clinical Research on Functional Nucleic Acid, Changsha Medical University, Changsha 410219, China
^d College of Chemistry and Materials Engineering, Hunan University of Arts and Science, Changde, Hunan 415000, China
^e School of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China

Received:2026-07-23 Published:2026-08-17
Contact: Rongnan Yi, Chao Wu, Longwu Ye, Weimin He
About author:
^† The authors contributed equally to this work.
Supported by:
The Hunan Provincial Natural Science Foundation(2026JJ90135); The Science and Technology Innovation Program of Hunan Province(2023RC4004); The Scientific Research Fund of Hunan Provincial Education Department(25A0703); The Scientific Research Fund of Hunan Provincial Education Department(23B0411); The Changsha Natural Science Foundation(104872)

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Abstract

The introduction of difluoromethylated units, particularly the alkoxycarbonyl difluoromethyl (CF₂CO₂R) group, into organic molecules has garnered substantial interest due to its capacity to enhance metabolic stability, lipophilicity, and bioavailability, while also serving as a versatile handle for downstream diversification. Phenanthridine derivatives represent a privileged class of N-heterocycles widely prevalent in natural products, pharmaceuticals, and functional materials. Although visible‑light photocatalysis has emerged as a powerful tool for constructing such fluorinated scaffolds, the majority of current protocols rely on external photosensitizers or stoichiometric additives, which raise concerns regarding cost, recyclability, and environmental sustainability. We herein report a visible-light-triggered self‑catalyzed tandem difluoromethylation/cyclization of 2-isocyanobiphenyls with alkyl bromodifluoroacetates under exogenous photocatalyst- and additive-free conditions. Under optimized conditions [415 nm LED irradiation, tetrahydrofuran (THF), 4  Å molecular sieves, argon, room temperature], a broad range of 2-isocyanobiphenyls bearing either electron‑donating or electron‑withdrawing groups were efficiently converted into the corresponding 6‑alkoxycarbonyl difluoromethyl phenanthridines in 68%~82% yields (20 examples). The reaction exhibits excellent functional‑group tolerance, accommodating halogens, trifluoromethyl, acetyl, ester, methoxy, and other valuable functionalities, and is also applicable to disubstituted substrates. Gram‑scale synthesis was achieved with 65% isolated yield, underscoring the practical utility of this approach. Mechanistic investigations revealed that the process is initiated by energy transfer from the photoexcited substrate or product to the bromodifluoroacetate, which induces homolytic C—Br bond cleavage to generate an alkoxycarbonyl difluoromethyl radical. This radical then undergoes regioselective addition to the isocyanide moiety, followed by intramolecular cyclization and oxidative dehydrogenation to afford the final product. This self-catalyzed strategy not only simplifies the reaction system and facilitates product isolation but also obviates the need for exogenous photocatalysts and additives, thereby aligning with green chemistry principles and offering a sustainable, atom-economical route to valuable fluorinated phenanthridines.

Key words: visible-light photocatalysis, self-catalysis, difluoromethylation reaction, 2-isocyanobiphenyls, phenanthridine

Cite this article

Jia Peng, Yun Yang, Yingli Cai, Rongnan Yi, Dongfang Jiang, Yucai Tang, Chao Wu, Longwu Ye, Weimin He. Visible-Light-Triggered Self-Catalyzed Tandem Difluoromethylation/Cyclization of 2-Isocyanobiphenyls with Alkyl Bromodifluoroacetates[J]. Acta Chimica Sinica, 2026, 84(9): 1399-1404.

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Fig. & Tab. 7

Scheme 1. Photocatalytic tandem difluoromethylation/cyclization of 2-isocyanobiaryls

Entry	Varying from the standard conditions	Yield^b/%
1	None	83
2	LED (405 nm, 10 W) was used	76
3	LED (385 nm, 10 W) was used	71
4	LED (425 nm, 10 W) was used	68
5	LED (455 nm, 10 W) was used	60
6	LED (415 nm, 8 W) was used	61
7	2-MeTHF was used	78
8	1,4-Dioxane was used	33
9	MeCN was used	39
10	DCE was used	N.R.
11	DMSO was used	N.R.
12	Without 4 Å MS	43
13	Without light	N.R.
14	Under Air	Trace

Table 1. Optimization of reaction conditions

Table 2. Scope of 2-isonitrile-biphenyl

Scheme 2. Gram-scale synthesis of 3a

Scheme 3. Control experiments

Figure 1. Light on/off experiment

Scheme 4. Proposed mechanism for visible-light-triggered self-catalyzed tandem difluoromethylation/cyclization of 2-isocyanobiphenyls with alkyl bromodifluoroacetates

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可见光触发2-异氰基联苯与二氟溴乙酸酯自催化二氟甲基化/环化串联反应

Visible-Light-Triggered Self-Catalyzed Tandem Difluoromethylation/Cyclization of 2-Isocyanobiphenyls with Alkyl Bromodifluoroacetates

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