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Topic: Buchwald-Hartwig coupling question  (Read 5589 times)

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Offline animanga008

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Buchwald-Hartwig coupling question
« on: September 03, 2010, 08:53:29 PM »
I was wondering if anyone knowledgeable in palladium chemistry could explain why I was getting a clean, high yield reaction when I couple a secondary amine with 4-bromobenzaldehyde versus coupling the same amine with Methyl 4-bromobenzoate? What is it about the aldehyde that is preventing me from getting a decent reaction?

Thanks

Offline MissPhosgene

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Re: Buchwald-Hartwig coupling question
« Reply #1 on: September 12, 2010, 10:18:32 AM »
Hi,

   If I were you I would look up the mechanism for that reaction in an organometallics book, for example. You may not find the exact one, but you should be able to piece things together. Then, I would look at the reactants and see how they can coordinate with the metal. You will find the answer there.

Best.
Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

Offline nox

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Re: Buchwald-Hartwig coupling question
« Reply #2 on: January 09, 2011, 03:51:20 PM »
Are you asking why your reaction ISN'T clean when you try to do the coupling with the aldehyde?

If so look at your reactants again. You have a secondary amine, and you're mixing that with an aldehyde (granted an aromatic aldehyde, but still an aldehyde nonetheless). That should set off some alarm bells.

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