Aromatic β-silylethenylation reactions via organogallium compounds

被引:34
作者
Kido, Y
Yoshimura, S
Yamaguchi, M [1 ]
Uchimaru, T
机构
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 9808578, Japan
[2] AIST, Agcy Ind Sci & Technol, Natl Inst Mat & Chem Res, Dept Phys Chem, Tsukuba, Ibaraki 3058565, Japan
关键词
D O I
10.1246/bcsj.72.1445
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the presence of GaCl3, silylethyne reacted electrophilically with aromatic hydrocarbons to give beta-silylethenylated arenes. The reaction proceeded via cationic species generated by the interaction of GaCl3 and silylethyne. High reactivity of the intermediate was demonstrated by the rapid reaction rate at -78 degrees C using close to the equimolar amount of the substrates. ipso-Substitution reaction took place with 1,2,3-trimethoxybenzene. Structures and properties of several organogallium compounds involved in the reactions are discussed.
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页码:1445 / 1458
页数:14
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