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 has been modified and expanded from the J. Chem. Ed. article linked below (J. Chem.