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Divergent Synthesis of N ‐Heterocycles by Merging Borane‐Mediated Cyclopropane Ring‐Opening and Hydride Abstraction
Author(s) -
Zhang ZiYu,
Ren Jie,
Zhang Ming,
Xu XiuFang,
Wang XiaoChen
Publication year - 2021
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202100056
Subject(s) - chemistry , borane , cyclopropane , hydride , substituent , ring (chemistry) , medicinal chemistry , stereochemistry , catalysis , combinatorial chemistry , organic chemistry , hydrogen
Main observation and conclusion Herein, we report the synthesis of N‐heterocycles by borane‐catalyzed dehydrogenative cyclization of 2‐cyclopropyl‐N,N‐dimethylanilines. Borane‐mediated cyclopropane ring‐opening and borane‐mediated hydride abstraction from an N‐methyl group are the key steps. The substituent at the cyclopropyl unit was found to greatly influence the reaction pathway and thus determined the major reaction product.