β-Silylethenylation of phenol with silylethyne using gallium trichloride

被引：9

作者：

Kobayashi, K ^{[1
]}

Arisawa, M ^{[1
]}

Yamaguchi, M ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan

来源：

INORGANICA CHIMICA ACTA | 1999年 / 296卷 / 01期

基金：

日本学术振兴会;

关键词：

gallium trichloride; phenol; beta-silylethenylation; carbometallation; carbogallation;

D O I：

10.1016/S0020-1693(99)00325-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Treatment of lithium phenoxide with silylethyne in the presence of GaCl3 gives o-(beta-silylethenyl)phenol in a high yield. The reaction involves carbogallation of phenoxygallium with silylethyne. The reaction of 2,6-disubstituted phenol with one of the substituents being t-butyl group gives ipso-substitution product. Organometallic compounds of gallium and tin, elements which sit diagonally in the periodic table, behave similarly in the carbometallation reaction. (C) 1999 Elsevier Science S.A. All rights reserved.

引用

页码：67 / 71

页数：5

共 4 条

[1] Ortho-vinylation reaction of phenols with ethyne [J].

Yamaguchi, M ;

Arisawa, M ;

Omata, K ;

Kabuto, K ;

Hirama, M ;

Uchimaru, T .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7298-7305

[2] ORTHO-VINYLATION AND ORTHO-ALKENYLATION OF PHENOLS [J].

YAMAGUCHI, M ;

HAYASHI, A ;

HIRAMA, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (03) :1151-1152

[3] CARBOMETALATION OF KETONE ENOLATES WITH 1-ALKYNES - AN ALKYLIDENATION REACTION OF SILYL ENOL ETHERS PROMOTED BY SNCL4-BU3N REAGENT [J].

YAMAGUCHI, M ;

HAYASHI, A ;

HIRAMA, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (08) :3362-3363

[4] Ethenylation of silyl enol ether with silylethyne [J].

Yamaguchi, M ;

Tsukagoshi, T ;

Arisawa, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (16) :4074-4075

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