2000年3月
Coupling reactions of alkynylsilanes mediated by a Cu(I) salt: Novel syntheses of conjugate diynes and disubstituted ethynes
JOURNAL OF ORGANIC CHEMISTRY
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- 巻
- 65
- 号
- 6
- 開始ページ
- 1780
- 終了ページ
- 1787
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.1021/jo991686k
- 出版者・発行元
- AMER CHEMICAL SOC
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.
- リンク情報
- ID情報
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- DOI : 10.1021/jo991686k
- ISSN : 0022-3263
- Web of Science ID : WOS:000086020300024