Buchwald-Hartwig Amination on amides?

11 October 2017 1 2K Report

I am thinking to do Buchwald-Hartwig amination with amide and bromo compound. Is this feasible (since BHA works good with secondary amines rather than primary amines)? if so, which catalyst I should use?

Thanks

Michael Rubin

Why BHA? You set up is ideal for Ullmann reaction (Copper-Catalyzed coupling), which should give very high yields. Check, for example, this reference:

Journal of Organic Chemistry, 76(4), 1180-1183; 2011

BHA works well with primary amines if you use Ni-based catalysts:

ChemCatChem, 6(12), 3474-3481; 2014

However, Pd also works with specially designed ligands:

Advanced Synthesis & Catalysis, 356(13), 2831-2837; 2014

Journal of Organometallic Chemistry, 841, 57-61; 2017

European Journal of Organic Chemistry, 2016(10), 1908-1914; 2016

RSC Advances, 3(27), 10707-10721; 2013

Also, with primary anilines (but not aliphatic amines) BHA should give you good results under standard reaction conditions.

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