Zeng Ming, Chen Jia-Le, Luo Xue, Zou Yan-Jiao, Liu Zhao-Ning, Dai Jun, Jiang Deng-Zhao, Li Jin-Jing
School of Pharmacy and Life Science, Jiujiang University, Jiujiang 332005, China.
College of Pharmacy, Jiamusi University, Jiamusi 154007, China.
Molecules. 2023 Nov 14;28(22):7587. doi: 10.3390/molecules28227587.
Aromatic ketones are important pharmaceutical intermediates, especially the pyridin-2-yl-methanone motifs. Thus, synthetic methods for these compounds have gained extensive attention in the last few years. Transition metals catalyze the oxidation of Csp-H for the synthesis of aromatic ketones, which is arresting. Here, we describe an efficient copper-catalyzed synthesis of pyridin-2-yl-methanones from pyridin-2-yl-methanes through a direct Csp-H oxidation approach with water under mild conditions. Pyridin-2-yl-methanes with aromatic rings, such as substituted benzene, thiophene, thiazole, pyridine, and triazine, undergo the reaction well to obtain the corresponding products in moderate to good yields. Several controlled experiments are operated for the mechanism exploration, indicating that water participates in the oxidation process, and it is the single oxygen source in this transformation. The current work provides new insights for water-involving oxidation reactions.
芳香酮是重要的药物中间体，尤其是吡啶 - 2 - 基 - 甲酮基序。因此，这些化合物的合成方法在过去几年中受到了广泛关注。过渡金属催化Csp - H氧化以合成芳香酮，这很引人注目。在此，我们描述了一种在温和条件下通过直接Csp - H氧化方法，以水为原料，由吡啶 - 2 - 基 - 甲烷高效铜催化合成吡啶 - 2 - 基 - 甲酮的方法。带有芳香环的吡啶 - 2 - 基 - 甲烷，如取代苯、噻吩、噻唑、吡啶和三嗪，能顺利进行反应，以中等至良好的产率得到相应产物。为探索反应机理进行了多项对照实验，结果表明水参与了氧化过程，并且它是该转化过程中的单一氧源。目前的工作为涉及水的氧化反应提供了新的见解。
