Synthesis of Polycyclic Amines through Mild Metal‐Free Tandem Cross‐Dehydrogenative Coupling/Intramolecular Hydroarylation of  N ‐Aryltetrahydroisoquinolines and Crotonaldehyde | Zendy

Wu Xiang | Zendy; Chen DianFeng | Zendy; Chen ShuSen | Zendy; Zhu YiFan | Zendy

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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.

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