Premium
Synthesis of Polycyclic Amines through Mild Metal‐Free Tandem Cross‐Dehydrogenative Coupling/Intramolecular Hydroarylation of N ‐Aryltetrahydroisoquinolines and Crotonaldehyde
Author(s) -
Wu Xiang,
Chen DianFeng,
Chen ShuSen,
Zhu YiFan
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403375
Subject(s) - chemistry , crotonaldehyde , intramolecular force , iminium , cycloaddition , enamine , catalysis , tandem , medicinal chemistry , amine gas treating , organic chemistry , materials science , composite material
A [4+2] cycloaddition reaction proceeding through tandem cross‐dehydrogenative coupling/intramolecular hydroarylation between N ‐aryltetrahydroisoquinolines and crotonaldehyde was developed by virtue of enamine–iminium catalysis, which enabled the rapid construction of ring‐fused tetrahydroquinolines. The first metal‐free catalytic oxidative coupling of γ‐selective C(sp 3 )–H bonds of crotonaldehyde was realized by using a secondary amine catalyst and 2,3‐dichloro‐5,6‐dicyanoquinone.