Chen Weiqiang, Li Hui-Jing, Cheng Yun-Fei, Wu Yan-Chao
Weihai Marine Organism & Medical Technology Research Institute, Harbin Institute of Technology, Weihai 264209, P.R. China.
Org Biomol Chem. 2021 Feb 25;19(7):1555-1564. doi: 10.1039/d0ob02579h.
C2-arylation of N-acyl pyrroles with aryl halides is developed for the first time using Pd(PPh3)4 as a catalyst in combination with Ag2CO3 under air, which allowed the application of a good compatibility catalytic system. This protocol provides a straightforward method for the preparation of valuable arylated pyrroles in moderate to good yields under the standard conditions with good substrate tolerance. Interestingly, while N-benzoyl pyrroles reacted well, the use of substrates with a thiophene or furan ring indicated that the thiophene and furan rings are more reactive than pyrrole for the present catalytic system.
首次开发了以Pd(PPh3)4为催化剂并结合Ag2CO3在空气中实现N-酰基吡咯与芳基卤化物的C2-芳基化反应,这使得一种具有良好兼容性的催化体系得以应用。该方法提供了一种直接的方式,可在标准条件下以中等至良好的产率制备有价值的芳基化吡咯,且底物耐受性良好。有趣的是,虽然N-苯甲酰基吡咯反应良好,但使用带有噻吩或呋喃环的底物表明,对于当前催化体系,噻吩环和呋喃环比吡咯更具反应活性。
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