Transition metal catalyzed cross-coupling reactions play a pivotal role in synthetic organic chemistry due to the impressive selectivity, high yields and overall control afforded by these reactions.  Despite the importance of these catalyzed reactions, they are not often incorporated into undergraduate organic chemistry teaching labs due to the air sensitive nature of many of the required catalysts and the prolonged set up times required to ensure the reactions are air-free.  Herein we describe our efforts to develop a Sonogashira cross-coupling reaction to be incorporated into a sophomore level second semester organic chemistry lab.  Using an electron deficient aryl iodide, trimethylsilyl acetylene and an inert atmosphere supplied using N<sub>2</sub> filled balloons, the reaction was able to be carried out and characterized in a four hour lab period (including a pre-lab lecture).  An analysis of the experimental cost will be presented as well.<br/>

Development of a practical Sonogashira experiment for implementation in an undergraduate organic chemistry lab

251st National Meeting (2016)

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