Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: johnnyd on May 26, 2010, 07:03:06 AM

Title: Buchwald-Hartwig Amination
Post by: johnnyd on May 26, 2010, 07:03:06 AM

Hi folks,

As far as I'm aware Buchwald-Hartwig couplings only work with an amine and aromatic halides. Am I wrong? Is it possible to couple vinyl halides to amines using this method? This would form an enamine that would presumably convert to an imine if possible. Either could be reduced in situ to give a substituted aliphatic amine no? Reductive amination type chemistry?

Any thoughts on this? I haven't seen an example in the literature with a vinyl halide. If it doesn't work, any ideas why?

Cheers.

Title: Re: Buchwald-Hartwig Amination
Post by: AC Prabakar on May 26, 2010, 09:24:00 AM

In general Buchwald-Hartwig couplings work with an amine and aromatic halides.But there are examples with vinyl bromide by using slightly modified method.(Refer the following paper:-M. C. Willis, J. Chauhan, W. G. Whittinham, Org. Biomol. Chem., 2005, 3, 3094-3095).

Yes your correct!It is possible to generate enamine!But i have to work on the remaining part of your question!!!!
Give me some time!!!!