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

被引：16

作者：

Wu, Xiang ^{[1
,2
]}

Chen, Dian-Feng ^{[1
,2
]}

Chen, Shu-Sen ^{[1
,2
]}

Zhu, Yi-Fan ^{[1
,2
]}

机构：

[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China

[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 03期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

Cross-coupling; Hydroarylation; Cycloaddition; Fused-ring systems; Polycycles; SP(3) C-H; VISIBLE-LIGHT PHOTOREDOX; CATALYZED OXIDATIVE CYANATION; CARBON BOND FORMATION; DIELS-ALDER REACTION; TERTIARY-AMINES; COUPLING REACTIONS; MOLECULAR-OXYGEN; NITROGEN ATOM; ASYMMETRIC ALKYNYLATION;

D O I：

10.1002/ejoc.201403375

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 gamma-selective C(sp(3))-H bonds of crotonaldehyde was realized by using a secondary amine catalyst and 2,3dichloro-5,6-dicyanoquinone.

引用

页码：468 / 473

页数：6

共 127 条

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