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Topic: Wacker oxidation on a molecule containing a tertiary amine  (Read 1075 times)

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Offline Bakterien

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Wacker oxidation on a molecule containing a tertiary amine
« on: September 01, 2023, 09:46:04 PM »
Hi

I'm about to do a simple Wacker oxidation (PdCl2, CuCl in DMF/H2O) of a terminal alkene. My molecule contains a tertiary amine and I'm worried it will form a complex with the Palladium. I checked scifinder but can't find a lot, usually it seems to work if the amine is electron deficient (aniline ect). I also have a secondary alcohol in my molecule.

Do you think the reaction will work fine ? Unfortunately I can't give you the structure.

Offline Guitarmaniac86

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Re: Wacker oxidation on a molecule containing a tertiary amine
« Reply #1 on: September 02, 2023, 02:41:55 AM »
Only one way to find out: try the reaction on small scale (20 to 50 mg) and see what happens by TLC/LCMS/NMR if you can isolate enough material.
Don't believe atoms, they make up everything!

Offline phth

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Re: Wacker oxidation on a molecule containing a tertiary amine
« Reply #2 on: September 02, 2023, 10:33:38 PM »
Hi

I'm about to do a simple Wacker oxidation (PdCl2, CuCl in DMF/H2O) of a terminal alkene. My molecule contains a tertiary amine and I'm worried it will form a complex with the Palladium. I checked scifinder but can't find a lot, usually it seems to work if the amine is electron deficient (aniline ect). I also have a secondary alcohol in my molecule.

Do you think the reaction will work fine ? Unfortunately I can't give you the structure.

amine could oxidize, but if it doesn't it should be fine. There obviously reactivity differences, but the buchwald-hartwig amination is a well known reaction. the palladium/copper orbitals form a poor linear combination with the amine orbitals. So usually at high temperature the bond formation and breakage are in fast enough equilibrium for the problem you are describing to not matter.

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