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Hydroalumination of silylacetylenes: a novel and highly stereoselective synthesis of (E)-telluro(silyl)ketene acetals and their applications in Sonogashira cross-coupling reactions |
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| Authors: | Cristiane Y. KawasokoCarlos E.D. Nazario,Amanda S. SantanaLuiz H. Viana,Gabriela R. HurtadoFrancisco A. Marques,Gustavo FrenschPaulo R. de Oliveira,Palimé cio G. Guerrero Jr.Diego B. Carvalho,Adriano C.M. Baroni |
| Affiliation: | a Departamento de Química, Universidade Federal do Mato Grosso do Sul, UFMS, Campo Grande, MS, Brazil b Departamento de Química, Universidade Federal do Paraná UFPR, Curitiba, PR, Brazil c Departamento de Química e Biologia, DAQBi, Universidade Tecnológica Federal do Paraná, UTFPR, Curitiba, PR, Brazil d Departamento de Fármacia-Bioquímica, Universidade Federal do Mato Grosso do Sul, UFMS, Campo Grande, MS, Brazil |
| Abstract: | The hydroalumination of silylacetylenes with DIBAL-H followed by the addition of n-butyllithium generated in situ the (Z)-β-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. |
| Keywords: | Hydroalumination ( boldFont" >Z)-β-Vinylorganosilane alanates Sonogashira cross-coupling Telluro(silyl)ketene acetals ( boldFont" >Z)-1,4-Diorganyl-2-tri(organyl)silyl-1-buten-3-ynes |
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