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An operationally simple sonogashira reaction for an undergraduate organic chemistry laboratory class

Cranwell, P., Peterson, A.M., Littlefield, B. and Russell, A. (2015) An operationally simple sonogashira reaction for an undergraduate organic chemistry laboratory class. Journal of Chemical Education. ISSN 0021-9584

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To link to this item DOI: 10.1021/acs.jchemed.5b00030

Abstract/Summary

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.

Item Type:Article
Refereed:Yes
Divisions:Interdisciplinary centres and themes > Chemical Analysis Facility (CAF)
Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:40101
Publisher:The American Chemical Society

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