区域选择性
化学
吲哚试验
共轭体系
衍生化
组合化学
催化作用
氢键
光化学
立体化学
有机化学
药物化学
分子
高效液相色谱法
聚合物
作者
Chao Zhou,Qi‐Chao Gan,Tai‐Ping Zhou,Tao Lei,Chen Ye,Xiao‐Jun He,Bin Chen,Heng Lu,Qian Wan,Rong‐Zhen Liao,Chen‐Ho Tung,Li‐Zhu Wu
标识
DOI:10.1002/anie.202116421
摘要
Site-selective N-1 and C-3 arylation of indole has been sought after because of the prevalent application of arylindoles and the intricate reactivities associated with the multiple sites of the N-unsubstituted indole. Represented herein is the first regioselective heteroarylation of indole via a radical-radical cross-coupling by visible-light irradiation. Steady and time-resolved spectroscopic and computational studies revealed that the hydrogen-bonding interaction of organic base and its conjugated acid, namely with indole and heteroarylnitrile, determined the reaction pathway, which underwent either proton-coupled electron-transfer or energy-transfer for the subsequent radical-radical cross-coupling, leading to the regioselective formation of C-3 and N-1 heteroarylation of indoles, respectively. The parallel methodologies for regioisomeric N-1 and C-3 heteroaryl indoles with good functional group compatibility could be applied to large-scale synthesis and late-stage derivatization of bioactive compounds under extremely mild reaction conditions.
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