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Metal‐Free Oxidative B−N Coupling of nido‐Carborane with N‐Heterocycles.
- Source :
-
Angewandte Chemie International Edition . Aug2019, Vol. 58 Issue 34, p11886-11892. 7p. - Publication Year :
- 2019
-
Abstract
- 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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *BORON
*BIOMEDICAL materials
*CARBORANES
*OXIDIZING agents
*OXIDATIVE coupling
Subjects
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 58
- Issue :
- 34
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 149246298
- Full Text :
- https://doi.org/10.1002/anie.201904940