Department of Chemistry, Indian Institute of Technology Kharagpur, 721302 Kharagpur, West Bengal, India.
Chem Commun (Camb). 2020 Apr 14;56(30):4240-4243. doi: 10.1039/d0cc00163e.
The insertion of a nitrile (-CN) group into arenes through the direct functionalization of the C(sp2)-Br bond is a challenging reaction. Herein, we report an organophotoredox method for the cyanation of aryl bromides using the organic photoredox catalyst 4CzIPN and tosyl cyanide (TsCN) as the nitrile source. A photogenerated silyl radical, via a single electron transfer (SET) mechanism, was employed to abstract bromine from aryl bromide to provide an aryl radical, which was concomitantly intercepted by TsCN to afford the aromatic nitrile. A range of substrates containing electron-donating and -withdrawing groups was demonstrated to undergo cyanation at room temperature in good yields.
将腈基（-CN）基团插入芳环中，通过 C(sp2)-Br 键的直接功能化，是一项具有挑战性的反应。在此，我们报告了一种使用有机光氧化还原催化剂 4CzIPN 和对甲苯磺酰基氰化物（TsCN）作为腈源，通过芳基溴的氰化的有机光氧化还原方法。光生硅自由基通过单电子转移（SET）机制，从芳基溴中抽溴以提供芳基自由基，该自由基与 TsCN 同时反应得到芳族腈。一系列含有供电子和吸电子基团的底物，在室温下以良好的收率进行氰化反应。
