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

Full Text: HTML

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 ...

Related Articles:

Enaminone ligand-assisted homo-and cross-coupling of terminal alkynes under mild conditions

[Liu, Yunyun; Wang, Chunping; Wang, Xiaobo; Wan, Jie-Ping Tetrahedron Letters, 2013 , vol. 54, # 30 p. 3953 - 3955]

Transition-metal-free homocoupling of 1-haloalkynes: a facile synthesis of symmetrical 1, 3-diynes

[Chen, Zhengwang; Jiang, Huanfeng; Wang, Azhong; Yang, Shaorong Journal of Organic Chemistry, 2010 , vol. 75, # 19 p. 6700 - 6703]

A mild CuI-catalyzed Glaser-type homo-coupling reaction using α, α-dibromo-β-dicarbonyl compounds as oxidants

[Fan, Xiaohui; Li, Na; Shen, Tong; Cui, Xiao-Meng; Lv, Hao; Zhu, Hong-Bo; Guan, Yong-Hong Tetrahedron, 2014 , vol. 70, # 2 p. 256 - 261]

A mild CuI-catalyzed Glaser-type homo-coupling reaction using α, α-dibromo-β-dicarbonyl compounds as oxidants

[Fan, Xiaohui; Li, Na; Shen, Tong; Cui, Xiao-Meng; Lv, Hao; Zhu, Hong-Bo; Guan, Yong-Hong Tetrahedron, 2014 , vol. 70, # 2 p. 256 - 261]

Synthesis of symmetrical 1, 3-butadiynes by homocoupling reactions of alkynylboronates mediated by a copper salt

[Nishihara, Yasushi; Okamoto, Masanori; Inoue, Yoshiaki; Miyazaki, Mikihiro; Miyasaka, Mitsuru; Takagi, Kentaro Tetrahedron Letters, 2005 , vol. 46, # 50 p. 8661 - 8664]

More Articles...