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Zhongming Yang Weijia Zhao Wei Liu Xing Wei Meng Chen Xiao Zhang Xiaolei Zhang Yong Liang Changsheng Lu Hong Yan 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2019,131(34):12012-12018
A general method for the oxidative substitution of nido‐carborane (7,8‐C2B9H12?) with N‐heterocycles has been developed by using 2,3‐dichloro‐5,6‐dicyanobenzoquinone (DDQ) as an oxidant. This metal‐free B?N coupling strategy, in both inter‐ and intramolecular fashions, gave rise to a wide array of charge‐compensated, boron‐substituted nido‐carboranes in high yields (up to 97 %) with excellent functional‐group tolerance under mild reaction conditions. The reaction mechanism was investigated by density‐functional theory (DFT) calculations. A successive single‐electron transfer (SET), B?H hydrogen‐atom transfer (HAT), and nucleophilic attack pathway is proposed. This method provides a new approach to nitrogen‐containing carboranes with potential applications in medicine and materials. 相似文献
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