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Rapid Synthesis of Fused N‐Heterocycles by Transition‐Metal‐Free Electrophilic Amination of Arene CH Bonds
Author(s) -
Gao Hongyin,
Xu QingLong,
Yousufuddin Muhammed,
Ess Daniel H.,
Kürti László
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.201309973
Subject(s) - electrophilic amination , amination , electrophile , chemistry , combinatorial chemistry , transition metal , electrophilic substitution , organic chemistry , stereochemistry , catalysis
Abstract We disclose an efficient and operationally simple protocol for the preparation of fused N‐heterocycles starting from readily available 2‐nitrobiaryls and PhMgBr under mild conditions. More than two dozen N‐heterocycles, including two bioactive natural products, have been synthesized using this method. A stepwise electrophilic aromatic cyclization mechanism was proposed by DFT calculations.