Thorpe-Ingold effect in copper(II)-catalyzed formal hydroalkoxylation-hydroarylation reaction of alkynols with indoles

被引：37

作者：

Patil, Nitin T. ^{[1
]}

Raut, Vivek S. ^{[1
]}

Kavthe, Rahul D. ^{[1
]}

Reddy, Vaddu V. N. ^{[1
]}

Raju, P. V. K. ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 2, Hyderabad 500607, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 47期

关键词：

Alkynes; Indoles; Copper catalyst; Hydroalkoxylation; Hydroarylation; GOLD-CATALYZED CYCLOISOMERIZATION; CYCLIC ALKENYL ETHERS; INTRAMOLECULAR CYCLIZATION; O-ALKYNYLBENZALDEHYDES; EXPEDITIOUS SYNTHESIS; ATOM ECONOMY; PLATINUM; MECHANISM; ACID;

D O I：

10.1016/j.tetlet.2009.09.057

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of Cu(OTf)(2) as a catalyst for tandem hydroalkoxylation-hydroarylation reaction of alkynes tethered with hydroxyl group is reported. The reaction proceeds at 60 degrees C or even at room temperature with 5 mol% catalyst loading and produces C-3-substituted indoles in good to high yields. The method was shown to be applicable to a broad range of indoles, containing electron-withdrawing and electron-donating substituents, and alkynol substrates bearing sterically demanding substituents in the tether. Interestingly, it was found that Thorpe-Ingold effect is operating for this cyclization reaction. Easy availability and low cost of Cu(OTf)(2) make this method attractive and amenable for large-scale synthesis compared to known literature methods. (C) 2009 Published by Elsevier Ltd

引用

页码：6576 / 6579

页数：4

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