Wang Xianjin, Li Haotian, Chen Yasu, Wang Ziqiang, Wu Xinxin, Zhu Chen
Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, State Key Laboratory of Synergistic Chem-Bio Synthesis, and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai, China.
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu, China.
Nat Commun. 2025 May 20;16(1):4702. doi: 10.1038/s41467-025-60011-0.
Fluorine-containing compounds hold pivotal importance in life sciences. Recent decades have witnessed significant research efforts toward developing practical fluorination methods. Radical-mediated decarboxylative fluorination has proven to be a robust approach for incorporating diverse monofluoroalkyl groups. Here we show a radical-mediated modular synthesis of alkyl fluorides through a decarboxylative-desulfonylative gem-difunctionalization under mild photochemical conditions. The multi-component reaction proceeds in a controlled sequence of radical decarboxylation and heteroaryl migration, governed by radical polarity and kinetic effects, resulting in a wide range of valuable alkyl fluorides. Two C-C bonds and one C-F bond are concurrently formed throughout the process. Both styrenes and aliphatic alkenes serve as suitable substrates for this transformation. Furthermore, this method can be applied to the incorporation of a monofluoroalkyl moiety into complex alkene molecules at a late stage.
含氟化合物在生命科学中具有至关重要的意义。近几十年来，人们为开发实用的氟化方法付出了巨大的研究努力。自由基介导的脱羧氟化反应已被证明是一种用于引入各种单氟烷基的可靠方法。在此，我们展示了一种在温和光化学条件下通过脱羧-脱磺酰基偕二官能化实现的自由基介导的模块化合成烷基氟化物的方法。多组分反应以自由基脱羧和杂芳基迁移的可控顺序进行，受自由基极性和动力学效应控制，从而得到多种有价值的烷基氟化物。在此过程中同时形成两个C-C键和一个C-F键。苯乙烯和脂肪族烯烃均可作为这种转化的合适底物。此外，该方法可应用于在后期将单氟烷基部分引入复杂烯烃分子中。
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