ERIC Number: EJ1067592
Record Type: Journal
Publication Date: 2015-Jun
Abstractor: As Provided
Reference Count: 9
An Operationally Simple Sonogashira Reaction for an Undergraduate Organic Chemistry Laboratory Class
Cranwell, Philippa B.; Peterson, Alexander M.; Littlefield, Benjamin T. R.; Russell, Andrew T.
Journal of Chemical Education, v92 n6 p1110-1114 Jun 2015
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.
Descriptors: Undergraduate Study, College Science, Science Instruction, Organic Chemistry, Science Laboratories, Laboratory Experiments, Science Experiments, Spectroscopy, Scientific Concepts
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Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Authoring Institution: N/A