Gold catalysis contra platinum catalysis in hydroarylation contra phenol synthesis

被引：54

作者：

Hashmi, A. Stephen K. ^{[1
]}

Kurpejovic, Elzen ^{[1
]}

Frey, Wolfgang ^{[1
]}

Bats, Jan W. ^{[1
]}

机构：

[1] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany

来源：

TETRAHEDRON | 2007年 / 63卷 / 26期

关键词：

alkynes; furans; gold; homogeneous catalysis; phenols; silanes;

D O I：

10.1016/j.tet.2007.02.108

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three silylated gamma-alkynylfurans were prepared and subjected to both gold and platinum catalysts. The TMS- and the TBDMS-substituted furans reacted. With AuCl3 and the binuclear [(Ph3PAu)(2)Cl][BF4] catalyst a hydroarylation of the alkyne was observed. Na[AuCl4] gave phenols as the product, but these were formed only after in situ desilylation of the starting material by the gold catalyst and thus the wrong isomer dominated. Only with PtCl2(MeCN)(2) phenols with a silyl group were formed. The TBDPS-substituted furan failed to react. Two alkynylsilanes were synthesized, but they also failed to react. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：5879 / 5885

页数：7

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