Grad School Post #2

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.

Beta-hydride elimination leads to enamines in this particular case, which ultimately form ketones in what is called the (get this) “Wacker oxidation.”

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.



  1. THAT question I actually DID get right! 🙂 It was a little less than 40 (~35). Apparently the trick was not to compare that hydrogen with the hydrogens in acetone…which would be a pretty dumb thing to do if you ask me, but hey, your boss loves making people look dumb…


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