Yb(OTf)3-catalyzed propargylation and allenylation of 1,3-dicarbonyl derivatives with propargylic alcohols:: one-pot synthesis of multi-substituted furocoumarin

被引：87

作者：

Huang, Wen ^{[1
]}

Wang, Jialiang ^{[1
]}

Shen, Quansheng ^{[1
]}

Zhou, Xigeng ^{[1
,2
]}

机构：

[1] Fudan Univ, Dept Chem, Shanghai Key Lab Mol Catalysis & Innovat Mat, Shanghai 200433, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2007年 / 63卷 / 47期

基金：

中国国家自然科学基金;

关键词：

propargylic alcohols; 1,3-dicarbonyl compounds; Coumarins; Lewis acid catalysis; substitution;

D O I：

10.1016/j.tet.2007.08.114

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient and mild Lewis acid-catalyzed coupling reaction of 1,3-dicarbonyl compounds with propargylic alcohols has been established. Selective propargylation or allenylation products are obtained depending on the nature of propargylic alcohols. In addition, catalytic quantities of Yb(OTf) 3 can also effectively promote the propargylation and allylation of 4-hydroxycoumarins at the 3-position. By applying this reaction as the key step, a multi-substituted furocoumarin can easily be synthesized in a one-pot procedure. The advantages of this method are broad scope, mild conditions, and easy handling since water is the only side product. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：11636 / 11643

页数：8

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