Well I just finished the test of death in chemistry 538, and I guess I feel good about it. Although if anybody knows the pKa of vinyl aldehyde at the double-bond hydrogen closer to the carbonyl group, I’d love to know. The suspense is killing me.
Grad school character #2 is Forrest Michael of the University of Washington. His group has worked recently with transition metal complexes, specifically palladium-centered complexes, to catalyze intermolecular hydroamination, a fancy name for “N-H adds to an alkene.” They found that the tridentate-ligand Pd complex shown above works wonderfully for this process. Monodentate ligands encourage beta-hydride elimination (shown below), but tridentate ligands are not nearly as easily displaced and thus can only catalyze hydroamination.
Wacker = BAD! The paper on this also includes a study of the effect of the nitrogen protecting group; interestingly, a tosyl protecting group leads to no product at all.