文献类型：期刊文献

英文题名：Pd-Catalyzed Vicinal Difunctionalization of Carboranes with Benzoxazoles, Indoles, and Anilines

作者：Zhu, Mengjie[1];Yu, Jiale[1];Jiang, Ruinian[1];Zhou, Zikang[1];Mu, Xin[1]

机构：[1]East China Univ Sci & Technol, Engn Res Ctr Pharmaceut Proc Chem, Sch Pharm, Minist Educ, Shanghai 200237, Peoples R China

年份：2025

卷号：28

期号：23

外文期刊名：EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:001458607700001)】；

基金：The authors are grateful for financial support from the Natural Science Foundation of Shanghai (22ZR1416700) and Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education.

语种：英文

外文关键词：benzoxazole; carborane; cross-coupling; difunctionalization; iodination

摘要：Icosahedral carboranes have a wide range of applications in medicinal chemistry, material science, and catalysis. Although various methods have been disclosed for functionalizing carborane structures, the methods to incorporate different types of heterocycles are still lacking. This limitation is likely due to the functional group incompatibility under previously reported reaction conditions. In this article, a streamlined protocol is presented to prepare a new class of vicinal difunctionalized carboranes containing benzoxazoles, NH heterocycles, and anilines. This method involves a direct cross-coupling between 9-bromo-m-carborane and benzoxazoles, thereby eliminating the necessity for preceding deprotonation of the acidic C2 proton present in benzoxazole. Subsequent regioselective iodination at the B(10) vertex of the carborane and the second cross-coupling reactions with diverse indoles and anilines result in the formation of the desired vicinal difunctionalized products.