Hydroalumination of silylacetylenes: a novel and highly stereoselective synthesis of (E)-telluro(silyl)ketene acetals and their applications in Sonogashira cross-coupling reactions

被引：3

作者：

Kawasoko, Cristiane Y. ^{[4
]}

Nazario, Carlos E. D. ^{[4
]}

Santana, Amanda S. ^{[4
]}

Viana, Luiz H. ^{[4
]}

Hurtado, Gabriela R. ^{[4
]}

Marques, Francisco A. ^{[3
]}

Frensch, Gustavo ^{[3
]}

de Oliveira, Paulo R. ^{[2
]}

Guerrero, Palimecio G. ^{[2
]}

Carvalho, Diego B., Jr. ^{[1
]}

Baroni, Adriano C. M. ^{[1
]}

机构：

[1] Univ Fed Mato Grosso do Sul, Dept Farm Bioquim, UFMS, Campo Grande, MS, Brazil

[2] Univ Tecnol Fed Parana, UTFPR, DAQBi, Dept Quim & Biol, Curitiba, Parana, Brazil

[3] Univ Fed Parana UFPR, Dept Quim, Curitiba, Parana, Brazil

[4] Univ Fed Mato Grosso do Sul, UFMS, Dept Quim, Campo Grande, MS, Brazil

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 46期

关键词：

Hydroalumination; (Z)-beta-Vinylorganosilane alanates; Sonogashira cross-coupling; Telluro(silyl)ketene acetals; (Z)-1,4-Diorganyl-2-tri(organyl)silyl-1-buten-3-ynes; IN-SITU FORMATION; DIISOBUTYLALUMINUM HYDRIDE; ORGANOMETALLIC COMPOUNDS; VERSATILE GENERATION; VINYLIC TELLURIDES; TERMINAL ALKYNES; Z-ENYNES; HALIDES; ACETYLENES; HYDRALUMINATION;

D O I：

10.1016/j.tetlet.2011.08.147

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hydroalumination of silylacetylenes with DIBAL-H followed by the addition of n-butyllithium generated in situ the (Z)-beta-vinylorganosilane alanates intermediates, which were trapped with butyltellurenyl bromide (C4H9TeBr), furnishing exclusively the (E)-1-butyltelluro-1-tri(organyl)silyl-2-organyl-1-alkenes in 45-70% yields. These telluro(silyl)ketene acetals were utilized as substrates in Sonogashira cross-coupling Pd-catalyzed reactions, furnishing the (Z)-1,4-diorganyl-2-tri(organyl)silyl-1-buten-3-ynes with total control of regio- and stereochemistry in 62-80% yield. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6067 / 6071

页数：5

共 30 条

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