Volume 43, Issue 7 pp. 798-804
Concise Report

Catalytic Difunctionalization of Alkenes under Visible Light Irradiation: Synthesis of Iminofuranones

Boyu Liu

Boyu Liu

Key Laboratory of Modern Analytical Science and Separation Technology of Fujian Province, School of Chemistry Chemical Engineering, and Environment, Minnan Normal University, Zhangzhou, Fujian, 363000 China

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Guangxian Chen

Guangxian Chen

Key Laboratory of Modern Analytical Science and Separation Technology of Fujian Province, School of Chemistry Chemical Engineering, and Environment, Minnan Normal University, Zhangzhou, Fujian, 363000 China

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Lele Zhang

Lele Zhang

Key Laboratory of Chemical Genomics of Guangdong Province, School of Chemical Biology and Biotechnology, Shenzhen Graduate School, Peking University, Shenzhen, Guangdong, 518055 China

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Feiwei Yan

Feiwei Yan

Key Laboratory of Modern Analytical Science and Separation Technology of Fujian Province, School of Chemistry Chemical Engineering, and Environment, Minnan Normal University, Zhangzhou, Fujian, 363000 China

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Feiming Li

Feiming Li

Key Laboratory of Modern Analytical Science and Separation Technology of Fujian Province, School of Chemistry Chemical Engineering, and Environment, Minnan Normal University, Zhangzhou, Fujian, 363000 China

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Zhixiong Cai

Zhixiong Cai

Key Laboratory of Modern Analytical Science and Separation Technology of Fujian Province, School of Chemistry Chemical Engineering, and Environment, Minnan Normal University, Zhangzhou, Fujian, 363000 China

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Mingqiang Huang

Mingqiang Huang

Key Laboratory of Modern Analytical Science and Separation Technology of Fujian Province, School of Chemistry Chemical Engineering, and Environment, Minnan Normal University, Zhangzhou, Fujian, 363000 China

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Lina Cai

Lina Cai

Key Laboratory of Modern Analytical Science and Separation Technology of Fujian Province, School of Chemistry Chemical Engineering, and Environment, Minnan Normal University, Zhangzhou, Fujian, 363000 China

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Shunyou Cai

Corresponding Author

Shunyou Cai

Key Laboratory of Modern Analytical Science and Separation Technology of Fujian Province, School of Chemistry Chemical Engineering, and Environment, Minnan Normal University, Zhangzhou, Fujian, 363000 China

Key Laboratory of Chemical Genomics of Guangdong Province, School of Chemical Biology and Biotechnology, Shenzhen Graduate School, Peking University, Shenzhen, Guangdong, 518055 China

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First published: 31 December 2024

Comprehensive Summary

Here, we show a cost-effective and environmentally friendly method for synthesizing iminofuranones using visible light and the photocatalyst 2-bromoanthraquinone. Our approach uses only oxygen as the oxidant, avoiding the need for additional transition metals and strong oxidizing agents. By employing a mixed solvent system of DMF and CHCl3 under ambient conditions, we have achieved highly diastereoselective conversions of various 2-vinyl benzamides and alkenyl amides into functionalized iminoisobenzofuranones and iminofuranones. This versatile process is broadly applicable and enables late-stage structural modifications of complex substrates with bioactive moieties.

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