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

doi:10.6023/A26070262

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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

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长沙 410219;
^d湖南文理学院化学与材料工程学院常德 415000;
^e南京林业大学化学工程学院南京 210037

投稿日期:2026-07-23
作者简介:^#共同第一作者.
基金资助:
湖南省自然科学基金(No. 2026JJ90135), 湖南省科技创新计划(No. 2023RC4004)资助项目, 湖南省教育厅科学研究项目(No. 25A0703, No.23B0411), 长沙市自然科学基金 (No.104872).

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

Jia Peng^a,#, Yun Yang^a,#, Ying-Li Cai^a, Rong-Nan Yi^b,*, Dong-Fang Jiang^c, Yu-Cai Tang^{d, e}, Chao Wu^a,*, Long-Wu Ye^a,*, Wei-Min He^a,*

^aSchool of Chemistry and Chemical Engineering, University of South China, Hengyang 421001;
^bKey Laboratory of Food & Environment & Drug Monitoring and Testing of Universities in Hunan Province, Hunan Police Academy, Changsha 410138;
^cHunan Provincial University Key Laboratory of the Fundamental and Clinical Research on Functional Nucleic Acid, Changsha Medical University, Changsha 410219;
^dCollege of Chemistry and Materials Engineering, Hunan University of Arts and Science, Changde 415000;
^eSchool of Chemical Engineering, Nanjing Forestry University, Nanjing 210037

Received:2026-07-23
Contact: *E-mail: yrn@hnu.edu.cn; chwu_chem@usc.edu.cn; longwuye@xmu.edu.cn; weiminhe@usc.edu.cn
About author:^#These authors contributed equally to this work.
Supported by:
Hunan Provincial Natural Science Foundation (No. 2026JJ90135), the Science and Technology Innovation Program of Hunan Province (No. 2023RC4004), the Scientific Research Fund of Hunan Provincial Education Department (No. 25A0703 and No.23B0411) and the Changsha Natural Science Foundation (No.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, 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, Ying-Li Cai, Rong-Nan Yi, Dong-Fang Jiang, Yu-Cai Tang, Chao Wu, Long-Wu Ye, Wei-Min He. Visible-Light-Triggered Self-Catalyzed Tandem Difluoromethylation/Cyclization of 2-Isocyanobiphenyls with Alkyl Bromodifluoroacetates[J]. Acta Chimica Sinica, doi: 10.6023/A26070262.

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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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