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General radical difluoromethylation using difluoroacetic anhydride via photoredox catalysis
Science China Chemistry ( IF 10.4 ) Pub Date : 2024-06-26 , DOI: 10.1007/s11426-023-1937-4
Meng He , Yankai Yang , Heng Zhang , Zhipeng Guan , Zhi-Bing Dong , Hong Yi , Aiwen Lei

CF2H-containing molecules play pivotal roles in diverse fields from medicinal chemistry to materials science. However, the application of existing CF2H reagents as a source of CF2H radical is limited by their reactivity and preparation. Herein, we develop a simple and general visible-light-catalyzed radical difluoromethylation reaction of alkenes, dienes, and heteroaromatics using commercially available, easy-to-handle, and low-cost difluoroacetic anhydride as the CF2H reagent. This scalable protocol enables the convenient synthesis of a range of CF2H-containing compounds under mild conditions, exhibiting a broad substrate scope and functional group tolerance. Potential applications are further demonstrated by gram-scale synthesis, sunlight experiments, derivatization experiments as well as the synthesis of bioactive molecules.



中文翻译:


使用二氟乙酸酐通过光氧化还原催化进行一般自由基二氟甲基化



CF 2 含氢分子在从药物化学到材料科学的各个领域中发挥着关键作用。然而,现有的CF 2 H试剂作为CF 2 H自由基源的应用受到其反应性和制备的限制。在此,我们使用市售、易于处理且低成本的二氟乙酸酐作为 CF 2 H,开发了一种简单且通用的可见光催化烯烃、二烯和杂芳烃的自由基二氟甲基化反应。试剂。这种可扩展的方案能够在温和条件下方便地合成一系列 CF 2 含 H 化合物,表现出广泛的底物范围和官能团耐受性。通过克级合成、阳光实验、衍生化实验以及生物活性分子的合成进一步证明了潜在的应用。

更新日期:2024-06-28
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