期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 34, 页码 11886-11892出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201904940
关键词
cage compounds; cross-coupling; heterocycles; reaction mechanisms; synthetic methods
资金
- NSFC [21820102004, 21531004, 21803030]
- National Thousand Young Talents Program
- Jiangsu Specially-Appointed Professor Plan
- NSF of Jiangsu Province in China [BK20170631]
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.
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