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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: orgeagle on April 07, 2006, 11:28:48 AM

Title: Buchwald-Hartwig N-aryl coupling?
Post by: orgeagle on April 07, 2006, 11:28:48 AM

I need add 4-chlorobenzene group to a secondary amine, can I use 4-chlorobenzenebromide by Buchwald-Hartwig cross coupling? I think both bromo and chloro will react with amine in the coupling reaction. How can I add a 4-chlorobenzene group to a secondary amine? Thank you very much for your suggestion.

Title: Re: Buchwald-Hartwig N-aryl coupling?
Post by: sw2672 on April 11, 2006, 05:31:00 PM

If you use the chelating arylphosphine ligand, aryl chloride would not react with amime, only aryl bromide could couple with amime.
BINAP or dppf as ligand would be great for the substrate you mentioned.