Gold(I)-catalyzed benzannulation of 3-hydroxy-1,5-enynes:: an efficient synthesis of substituted tetrahydronaphthalenes and related compounds

被引：55
|
作者：
Grise, Christiane M. [1 ]
Rodrigue, Eric M. [1 ]
Barriault, Louis [1 ]
机构：
[1] Univ Ottawa, Dept Chem, Ctr Catalysis & Innovat, Ottawa, ON K1N 6N5, Canada
来源：
TETRAHEDRON | 2008年 / 64卷 / 05期
基金：
加拿大创新基金会; 加拿大自然科学与工程研究理事会;
关键词：
D O I：
10.1016/j.tet.2007.10.084
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report a novel gold(l)-catalyzed benzannulation of 3-hydroxy-1,5-enynes to prepare tetrahydronaphthalenes. The reaction is catalyzed by 2.5 mol % Ph3PAuCl and 2.5 mol % AgOTf in dichloromethane. We discovered that this process can be also catalyzed by I mol % Ph3PAuCl and I mol % TfOH. To the best of our knowledge, this constitutes the first report of an active gold catalyst generated from Au(PPh3)Cl and triflic acid. This mild process is compatible with a variety of functional groups and proves to be an effective method to synthesize various metasubstituted aromatic rings in good yields. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：797 / 808
页数：12
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