Pan Liuyan, Chen Shengwei, Wu Dongfang, Shao Jian, Bao Xiaofeng, Liu Gong-Qing
Nantong Key Laboratory of Small Molecular Drug Innovation, School of Pharmacy, Nantong University, Nantong 226019, China.
Molecules. 2025 Apr 22;30(9):1870. doi: 10.3390/molecules30091870.
3-Chalcogenylindoles serve as crucial building blocks in organic synthesis and pharmaceutical chemistry. Herein, we describe a simple and general synthesis of 3-chalcogenylindoles through the direct C-H chalcogenation of indoles using -selenophthalimide and -sulfenylsuccinimide as chalcogenation reagents in the presence of CuBr as the catalyst. The reactions were carried out in CHCl at room temperature under an air atmosphere with a low loading of catalyst, and a wide range of 3-selenylindoles and 3-thioindoles were obtained in good yields. Various functionalities, namely, methyl, methoxy, halo, ester, cyano, trifluoromethyl, and formyl groups on indoles, have shown amenability to the developed reaction. A mechanism involving the activation of the chalcogenation agent through CuBr coordination with the amide carbonyl group is proposed.
3-硫属元素吲哚是有机合成和药物化学中的关键结构单元。在此，我们描述了一种简单通用的合成3-硫属元素吲哚的方法，即在溴化铜作为催化剂的存在下，使用邻苯二甲酰亚胺硒和琥珀酰亚胺硫作为硫属化试剂，通过吲哚的直接C-H硫属化反应来合成。反应在空气氛围下于室温在氯仿中进行，催化剂负载量低，可高产率地得到多种3-硒代吲哚和3-硫代吲哚。吲哚上的各种官能团，即甲基、甲氧基、卤素、酯基、氰基、三氟甲基和甲酰基，都适用于所开发的反应。我们提出了一种通过溴化铜与酰胺羰基配位来活化硫属化试剂的机理。
