Liu Hongxin, Yu Zhichao, Li Bin, Wang Baiquan
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, People's Republic of China.
J Org Chem. 2024 Sep 20;89(18):13429-13437. doi: 10.1021/acs.joc.4c01581. Epub 2024 Sep 3.
The addition of C-H bonds to isocyanates catalyzed by transition metals is a highly auspicious methodology for providing synthetically and biologically important amides. However, the substrates are limited to C(sp)-H bonds. In this work, an efficient manganese(I)-catalyzed direct addition reaction of C(sp)-H bonds of 8-methylquinolines to aryl isocyanates has been developed, leading to the synthesis of various α-quinolinyl amide compounds in moderate to high yields. The reaction has a broad range of substrates and a good functional group tolerance. A possible mechanism is proposed based on the experimental results.
过渡金属催化的异氰酸酯与碳氢键的加成反应是一种极具前景的方法，可用于合成具有重要合成和生物学意义的酰胺。然而，底物仅限于碳（sp）-氢键。在这项工作中，已经开发出一种高效的锰（I）催化的8-甲基喹啉的碳（sp）-氢键与芳基异氰酸酯的直接加成反应，以中等至高产率合成了各种α-喹啉基酰胺化合物。该反应具有广泛的底物范围和良好的官能团耐受性。基于实验结果提出了一种可能的机理。
