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Facile Synthesis of N ‐Carboranyl Amines through an ortho ‐Carboryne Intermediate
Author(s) -
Cheng Ruofei,
Zhang Jie,
Zhang Jiji,
Qiu Zaozao,
Xie Zuowei
Publication year - 2016
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.201507952
Subject(s) - chemistry , medicinal chemistry , combinatorial chemistry
The efficient o ‐carboryne precursor 1‐Li‐2‐OTf‐ o ‐C 2 B 10 H 10 reacts with lithium amides at room temperature to give a series of N ‐carboranyl amines in moderate to high isolated yields. This reaction is compatible with a broad substrate scope from primary to secondary, alkyl to aryl amines. The reaction mechanism is also proposed on the basis of experimental results and DFT calculations. This represents the first general and efficient method for the synthesis of 1‐NR 1 R 2 ‐ o ‐carboranes.