Coupling reactions of alkynylsilanes mediated by a Cu(I) salt: Novel syntheses of conjugate diynes and disubstituted ethynes

被引：250

作者：

Nishihara, Y ^{[1
]}

Ikegashira, K ^{[1
]}

Hirabayashi, K ^{[1
]}

Ando, J ^{[1
]}

Mori, A ^{[1
]}

Hiyama, T ^{[1
]}

机构：

[1] Tokyo Inst Technol, Resources Utilizat Res Lab, Yokohama, Kanagawa 2268503, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 06期

关键词：

D O I：

10.1021/jo991686k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of 1-trimethylsilylalkyne with copper(I) chloride in a polar solvent, DMF, at 60 OC under an aerobic conditions smoothly undergoes home-coupling to give the corresponding symmetrical 1,3-butadiynes in 70-99% yields. In addition, (arylethynyl)trimethylsilanes are found to couple with aryl triflates and chlorides in the presence of Cu(I)/Pd(0) (10 mol %/5 or 10 mol %) cocatalyst system to give the corresponding diarylethynes in 49-99% yields. The cross-coupling reaction is applied to a one-pot synthesis of the corresponding unsymmetrical diarylethynes from (trimethylsilyl)ethyne via sequential Sonogashira-Hagihara and the present cross-coupling reactions using two different aryl triflates. The reactions of (arylethynyl)trimethylsilanes with aryl(chloro)ethynes in the presence of 10 mol % of CuCl also yield the corresponding unsymmetrical 1,3-butadiynes in 43-97% yields.

引用

页码：1780 / 1787

页数：8

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