College of Chemistry, Green Catalysis Center, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, P R China.
Org Biomol Chem. 2020 Jun 24;18(24):4628-4637. doi: 10.1039/d0ob00586j.
A simple and efficient protocol for palladium-catalyzed C8-H alkoxycarbonylation of 1-naphthylamine derivatives with alkyl chloroformates has been developed, exhibiting broad functional group tolerance, high regioselectivity, and oxidant-free conditions. Furthermore, the reaction features its ease of further functionalization and transformation. For example, the concise synthesis of one BET bromodomain inhibitor was accomplished via benz[cd]indol-2(1H)-one after multistep transformations from the obtained alkoxycarbonylation product. In addition, the control experiments suggest that the reaction might involve a radical process and the C-H bond cleavage might not be involved in the rate-determining step.
已开发出一种简单高效的钯催化 1-萘胺衍生物与氯甲酸烷基酯的 C8-H 烷氧基羰基化反应的方法，该方法具有广泛的官能团容忍性、高区域选择性和无氧化剂条件。此外，该反应具有易于进一步官能化和转化的特点。例如，通过多步转化从获得的烷氧基羰基化产物，简洁地合成了一种 BET 溴结构域抑制剂苯并[cd]吲哚-2(1H)-酮。此外，对照实验表明，该反应可能涉及自由基过程，C-H 键的断裂可能不在速率决定步骤中。
