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An Unexpected Construction of 2‐Arylquinolines from N ‐Cinnamylanilines through sp 3 CH Aerobic Oxidation Induced by a Catalytic Radical Cation Salt
Author(s) -
Liu Fang,
Yu Liangliang,
Lv Shiwei,
Yao Junjun,
Liu Jing,
Jia Xiaodong
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500574
Subject(s) - chemistry , aniline , imine , salt (chemistry) , aromatization , intramolecular force , catalysis , decomposition , medicinal chemistry , radical ion , photochemistry , stereochemistry , organic chemistry , ion
An unexpected reaction of cinnamylanilines was achieved through the radical cation salt‐induced aerobic oxidation of sp 3 CH bonds, providing a series of 2‐arylquinolines. The mechanistic study shows that the cinnamylaniline was oxidized to an imine, which was attacked by the aniline generated through decomposition of the corresponding imine. After further intramolecular cyclization and aromatization, 2‐arylquinolines were obtained. This reaction provides a new method to construct 2‐arylquinolines from readily accessible starting materials.