An Operationally Simple Sonogashira Reaction for an Undergraduate Organic Chemistry Laboratory Class

作者：Cranwell Philippa B^*; Peterson Alexander M; Littlefield Benjamin T R; Russell Andrew T

来源：Journal of Chemical Education, 2015, 92(6): 1110-1114.

DOI：10.1021/acs.jchemed.5b00030

• Second-Year Undergraduate
• Organic Chemistry
• Laboratory Instruction
• Hands-On Learning/Manipulatives
• Alkynes
• Aromatic Compounds
• Catalysis
• IR Spectroscopy
• NMR Spectroscopy
• Transition Elements

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.

• 出版日期2015-6