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

doi:10.6023/A26070262

化学学报 ›› 2026, Vol. 84 ›› Issue (9): 1399-1404.DOI: 10.6023/A26070262 上一篇下一篇

研究通讯

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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1. Supporting Information-A26070262.pdf(4655KB)

摘要/Abstract

可见光催化将光能转化为化学能, 在温和条件下实现化学键的断裂与重组, 完成诸多传统热化学路径难以驱动的转化, 具有环境友好及官能团耐受性高等优点, 已在复杂功能分子合成中展现出显著的催化效率和工业应用潜力. 然而, 现有方法多依赖外源光催化剂, 存在回收困难或活性不足等问题. 为此, 本文以2-异氰基联苯为底物、二氟溴乙酸酯为烷氧基羰基二氟甲基化试剂, 利用底物和产物自身充当光敏剂, 发展了一种无需外源光敏剂及添加剂的可见光触发自催化烷氧基羰基二氟甲基化/环化串联反应, 以68%~82%的分离收率获得20种6-烷氧基羰基二氟甲基菲啶化合物, 并可实现克级规模制备. 该策略不仅简化了反应体系并降低了分离难度, 同时具有操作简便和底物适用范围广等优势, 为6-烷氧基羰基二氟甲基菲啶类化合物的绿色可持续合成提供了新路径, 高度契合绿色化学的原子经济性和步骤经济性原则.

关键词: 可见光催化, 自催化, 二氟甲基化反应, 2-异氰基联苯, 菲啶

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

引用此文

彭佳, 杨云, 蔡迎丽, 易荣楠, 姜东方, 唐裕才, 吴超, 叶龙武, 何卫民. 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[J]. 化学学报, 2026, 84(9): 1399-1404.

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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图/表 7

图式1. 光催化2-异氰基联苯的二氟甲基化/环化串联反应

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

表1. 反应条件优化a

Table 1. Optimization of reaction conditions

表2. 2-异氰基联苯反应范围a

Table 2. Scope of 2-isonitrile-biphenyl

图式2. 克级合成3a

Scheme 2. Gram-scale synthesis of 3a

图式3. 控制实验

Scheme 3. Control experiments

图1. 光源开/关实验

Figure 1. Light on/off experiment

图式4. 可见光驱动2-异氰基联苯与二氟溴乙酸酯自催化二氟乙酰基化/环化串联反应的可能机理

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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