Copper-Mediated Fluorination of Aryl Iodides

The synthesis of aryl fluorides has been studied intensively because of the importance of aryl fluorides in pharmaceuticals, agrochemicals, and materials. The stability, reactivity, and biological properties of aryl fluorides can be distinct from those of the corresponding arenes. Methods for the synthesis of aryl fluorides, however, are limited. We report the conversion of a diverse set of aryl iodides to the corresponding aryl fluorides. This reaction occurs with a cationic copper reagent and silver fluoride. Preliminary results suggest this reaction is enabled by a facile reductive elimination from a cationic arylcopper­(III) fluoride.鉴于芳基氟化物(aryl fluoride)在制药、农药及材料领域的重要应用价值，其合成方法已得到广泛深入的研究。芳基氟化物的稳定性、反应活性与生物学特性，与对应的芳烃(arene)存在显著差异。然而，当前可用于合成芳基氟化物的方法仍较为有限。本研究报道了将一系列结构多样的芳基碘化物(aryl iodide)转化为对应芳基氟化物的反应，该反应以阳离子铜试剂(cationic copper reagent)与氟化银(silver fluoride)为反应试剂得以实现。初步研究结果表明，该反应通过阳离子芳基铜(III)氟化物(cationic arylcopper(III) fluoride)发生便捷的还原消除(reductive elimination)过程得以启动。