It’s time for a confession.  Before last Friday, I had never run a catalytic hydrogenation with palladium (or Pd(OH)2) on charcoal.  I’ve done reductive aminations, amide couplings, and loads of Huisgen cycloadditions, but have never needed to reduce a pretty little azide to an amine or remove a pesky alkene.

So, before I got started I read up on the “literature.”  A few years ago, Daniel Sejer at the Curly Arrow dissected catalytic hydrogenation over three different blogpostsThe first post details how add the palladium without starting a fire and other fun basics, while the second and third posts are for troubleshooting.  Check out the comments too, for loads of good tips (milkshake shows up each time, brimming with ridiculously good advice). [1]

 

[1] For the human interest angle, I’ve finished the workup and my NMR looks promising.  It’s a crowded spectra, but I’m cautiously optimistic.

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