Premium
Regioselective Insertion of o ‐Carborynes into the α‐CH Bond of Tertiary Amines: Synthesis of α‐Carboranylated Amines
Author(s) -
Zhao Da,
Zhang Jiji,
Xie Zuowei
Publication year - 2014
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.201409141
Subject(s) - regioselectivity , chemistry , intramolecular force , tertiary amine , nucleophile , nucleophilic addition , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Abstract o ‐Carboryne can undergo α‐CH bond insertion with tertiary amines, thus affording α‐carboranylated amines in very good regioselectivity and isolated yields. In this process, the nucleophilic addition of tertiary amines to the multiple bond of o ‐carboryne generates a zwitterionic intermediate. An intramolecular proton transfer, followed by a nucleophilic attack leads to the formation of the final product. Thus, regioselectivity is highly dependent upon the acidity of α‐CH proton of tertiary amines. This approach serves as an efficient methodology for the preparation of a series of 1‐aminoalkyl‐o‐carboranes.