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Catalyst-free and visible light promoted trifluoromethylation and perfluoroalkylation of uracils and cytosines†
Chemical Communications ( IF 4.9 ) Pub Date : 2018-10-22 00:00:00 , DOI: 10.1039/c8cc07759b
Yang Huang 1, 2, 3, 4, 5 , Yun-Yun Lei 1, 2, 3, 4, 5 , Liang Zhao 1, 2, 3, 4, 5 , Jiwei Gu 5, 6, 7, 8, 9 , Qiuli Yao 1, 2, 3, 4, 5 , Ze Wang 1, 2, 3, 4, 5 , Xiao-Fei Li 1, 2, 3, 4, 5 , Xingang Zhang 5, 6, 7, 8, 9 , Chun-Yang He 1, 2, 3, 4, 5
Affiliation  

Fluoroalkylated enaminones, such as trifluridine and 5-trifluoromethyluracil, have widespread applications in pharmaceuticals and agrochemicals. Although these kinds of pharmaceutical agent often bear CF3 and perfluoroalkyl motifs in the core structure, access to such analogues typically requires multi-step synthesis. Here, we report a mild, metal-free and operationally simple strategy for the direct perfluoroalkylation of uracils, cytosines and pyridinones through a visible-light induced pathway from perfluoroalkyl iodides. This photochemical transformation features synthetic simplicity, mild reaction conditions without any photoredox catalyst, and high functional group tolerance, providing a facile route for applications in medicinal chemistry.

中文翻译:

不含催化剂的可见光可促进尿嘧啶和胞嘧啶的三氟甲基化和全氟烷基化

氟烷基化的烯胺酮,例如三氟吡啶和5-三氟甲基尿嘧啶,在药物和农用化学品中具有广泛的应用。尽管这类药物通常在核心结构中带有CF 3和全氟烷基基序,但要获得此类类似物通常需要多步合成。在这里,我们报告了一种温和,无金属且操作简单的策略,可通过可见光诱导的全氟烷基碘化物途径,直接对尿嘧啶,胞嘧啶和吡啶酮进行全氟烷基化。这种光化学转化具有合成简单,反应条件温和,无任何光氧化还原催化剂以及高官能团耐受性的特点,为在药物化学中的应用提供了便捷的途径。
更新日期:2018-10-22
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