I wanted a modern organometallic experiment showing the utility of Pd for coupling reactions. Students attempted a variety of reaction conditions during the spring of 2007 and 2008. Eventually, we were able to get the reaction to work with a variety of primary amines (linear, cyclohexylamine) and t-butylamine. Yields are not great (40-80%) and this experiment needs some optimization. However, products were observed by GC-MS and NMR.
This experiment is air-sensitive, but not enormously so. The most sensitive reagent is the NaOtBu, which could be weighed in air in a pinch. We use a glove box since we have one. We store the Pd complexes under N2 after use.
Schlenk line, Ar balloons or glove box
Schlenk glassware, standard organic glassware
temperature controlled oil bath or heating mantle and thermometer.
I usually turn off the students reactions after 18-24 hours, let them cool down, quench them with ether and store them in the 2-neck flasks until the following week where students work up the reaction and analyze by NMR and GC-MS. We don't purify the compounds by column chromatography, but that could be added easily.
I would normally grade on purity and yield of the isolated compound, as well as experimental technique, but since we are still optimizing the conditions, I give students the benefit of the doubt.