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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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 (C 4H9TeBr), 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. © 2011 Elsevier Ltd. All rights reserved.

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Kawasoko, C. Y., Nazario, C. E. D., Santana, A. S., Viana, L. H., Hurtado, G. R., Marques, F. A., … Baroni, A. C. M. (2011). Hydroalumination of silylacetylenes: A novel and highly stereoselective synthesis of (E)-telluro(silyl)ketene acetals and their applications in Sonogashira cross-coupling reactions. Tetrahedron Letters, 52(46), 6067–6071. https://doi.org/10.1016/j.tetlet.2011.08.147

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