文献类型：期刊文献

英文题名：A Pd-catalyzed route to carborane-fused boron heterocycles

作者：Zhu, Mengjie[1];Wang, Puzhao[1];Wu, Zhengqiu[2];Zhong, Yangfa[1];Su, Laiman[5];Xin, Yuquan[1];Spokoyny, Alexander M.[3,4];Zou, Chao[2];Mu, Xin[1]

机构：[1]East China Univ Sci & Technol, Engn Res Ctr Pharmaceut Proc Chem, Sch Pharm, Minist Educ, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]Songshan Lake Mat Lab, Frontier Res Ctr, Funct Coordinat Mat Grp, Dongguan 523808, Guangdong, Peoples R China;[3]Univ Calif Los Angeles, Dept Chem & Biochem, 607 Charles E Young Dr East, Los Angeles, CA 90095 USA;[4]Univ Calif Los Angeles, Calif Nanosyst Inst CNSI, Los Angeles, CA 90095 USA;[5]East China Univ Sci & Technol, Sch Biotechnol, 130 Meilong Rd, Shanghai 200237, Peoples R China

年份：2024

卷号：15

期号：27

起止页码：10392

外文期刊名：CHEMICAL SCIENCE

收录：;EI(收录号：20242516265677);WOS:【SCI-EXPANDED(收录号:WOS:001240602200001)】；

基金：Support for this study was provided by Natural Science Foundation of Shanghai (22ZR1416700) and start-up fund from Songshan Lake materials Laboratory (Y1D1061C11). We thank Prof. Guosheng Liu and Dr Haoyang Wang from Shanghai Institute of Organic Chemistry for fruitful discussions. We are thankful for the financial support from Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education.

语种：英文

外文关键词：Aniline - Catalysis

摘要：Due to the expanding applications of icosahedral carboranes in medicinal and materials chemistry research, their functionalizations have become one of the central themes in boron-rich cluster chemistry. Although several strategies for incorporating nitrogen-containing nucleophiles on a single boron vertex of the icosahedral carboranes (C2B10H12) have been developed, methods for preparing clusters with vicinal B-N moieties are still lacking. The steric bulk of icosahedral carboranes and disparate electronic and steric nature of the N-containing groups have rendered the vicinal diamination challenging. In this article, we show how a developed Pd-catalyzed process is used to incorporate an array of NH-heterocycles, anilines, and heteroanilines with various electronic and steric profiles onto the vicinal boron vertices of a meta-carborane cluster via sequential or one-pot fashion. Importantly, oxidative cyclizations of the cross-coupling products with indoles and pyrroles appended to boron vertices generate a previously unknown class of all-boron-vertex bound carborane-fused six- and seven-membered ring heterocycles. Photophysical studies of the meta-carborane-fused heterocycles show that these structures can exhibit luminescence with high quantum yields and are amenable to further manipulations. A Pd-catalyzed cross-coupling system has been developed to achieve vicinal diamination of 9,10-dibromo-carborane with NH-heterocycles and anilines. These products can be further converted to carborane-fused six- and seven-membered heterocycles.