An Operationally Simple Sonogashira Reaction for an Undergraduate Organic Chemistry Laboratory Class
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Philippa B. Cranwell [1] ; Alexander M. Peterson [1] ; Benjamin T. R. Littlefield [1] ; Andrew T. Russell [1]
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[1] University of Reading
University of Reading
Reino Unido
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- Localización: Journal of chemical education, ISSN 0021-9584, Vol. 92, Nº 6, 2015, págs. 1110-1114
- Idioma: inglés
- Texto completo no disponible (Saber más ...)
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Resumen
An operationally simple, reliable, and cheap Sonogashira reaction suitable for an undergraduate laboratory class that can be completed within a day-long (8 h) laboratory session has been developed. Cross-coupling is carried out between 2-methyl-3-butyn-2-ol and various aryl iodides using catalytic amounts of bis(triphenylphosphine)palladium(II) dichloride, with copper(I) iodide as a cocatalyst, in triethylamine at room temperature, so a range of products can be prepared within a single group and results compared. The coupling itself is usually complete within 1.5 h and is easily monitored by TLC, leaving up to 6 h for purification and characterization. Purification is by “mini flash column chromatography” through a plug of silica encased in the barrel of a plastic syringe, so the procedure is amenable to large class sizes.
