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

Y Nishihara, K Ikegashira, K Hirabayashi…

Index: Nishihara, Yasushi; Ikegashira, Kazutaka; Hirabayashi, Kazunori; Ando, Jun-Ichi; Mori, Atsunori; Hiyama, Tamejiro Journal of Organic Chemistry, 2000 , vol. 65, # 6 p. 1780 - 1787

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Citation Number: 251

Abstract

Reaction of 1-trimethylsilylalkyne with copper (I) chloride in a polar solvent, DMF, at 60° C under an aerobic conditions smoothly undergoes homo-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 ...

~77%

~83%

~68%

~85%

~68%

~89%

~63%

~74%

~21%

~51%

~64%

~43%

~62%

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