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Metal‐Free Oxidative B−N Coupling of nido ‐Carborane with N‐Heterocycles
Author(s) -
Yang Zhongming,
Zhao Weijia,
Liu Wei,
Wei Xing,
Chen Meng,
Zhang Xiao,
Zhang Xiaolei,
Liang Yong,
Lu Changsheng,
Yan Hong
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201904940
Subject(s) - carborane , intramolecular force , chemistry , boron , density functional theory , hydrogen atom , oxidative coupling of methane , metal , nucleophile , computational chemistry , nucleophilic substitution , medicinal chemistry , oxidative phosphorylation , stereochemistry , group (periodic table) , organic chemistry , biochemistry , methane , catalysis
A general method for the oxidative substitution of nido ‐carborane (7,8‐C 2 B 9 H 12 − ) 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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