Aldehydes to esters in one step. Palladium catalyzed. Acetone(!) as the oxidant. Brilliant on so many levels.

Esters from aldehydes

Org. Lett. 2013, ASAP (DOI: 10.1021/ol303298g)

I admire their honesty about the fact that the stumbled upon this protocol when identifying byproducts from other planned reactions, and then realized that this might be useful for scientists outside their own field. That is how you roll!

Once again, serendipity FTW.

 

2 Responses to Nice one, Molander

  1. Phillip says:

    Slightly remeniscent of the Meerwein-Ponndorf-Verley reduction/Oppenauer oxidation type reactions, using a sacrificial ketone as oxidant, but extending out to make the ester.

    Would be interested to see a proposed catalytic cycle for that one – doesn’t look particularly trivial…

    • SN says:

      I imagine the aldehyde + alcohol makes a hemiacetal. The free OH interacts with Pd to make a new Pd-O bond at the expense of one of the acetate ligands. Beta-hydride elimination gives the ester and a Pd-H which can reduce the acetone.

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