Pd-catalyzed amination in a polar medium: rate enhancement, convenient product isolation, and tandem Suzuki cross-coupling

A catalytic system utilizing a polar medium for the Pd-catalyzed amination reaction is described. This system utilizes Pd[P(t-Bu)3]2 and a weak base and displays a modest rate enhancement compared to similar existing protocols. Significant functional group tolerance is observed in both amine and aryl halide, including carboxylates, carbamates, nitriles, amides, and esters. Product isolation after filtration and automated reverse-phase chromatography readily permits parallel synthetic approaches if desired.