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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201507952
Subject(s) - chemistry , lithium (medication) , substrate (aquarium) , aryl , medicinal chemistry , alkyl , primary (astronomy) , reaction mechanism , stereochemistry , organic chemistry , catalysis , medicine , oceanography , physics , astronomy , endocrinology , geology
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.