Sunday, November 16, 2008

Pd catalyzed coupling of halides with enolates

Some players:
James Cook, Buchwald, Hartwig,
Josep Bonjoch...

progress:
intermolecular: enolates from ketone, ester, amide, nitrile; halides can be Ar-X, vinyl bromide.
intramolecular: enolates from ketone, ester, nitrile, halides can be Ar-x, vinyl bromide/iodide.

You may notice intramolecular amide coupling is missing.
The reason is obvious that strong base is needed to deprotonate the amide which can cause server side reactions. In the intermolecuar situation, this can be avoided by exchange the strong lithium enolate of amide with Zinc enolate as done by Hartwig.

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