Enolizable Ketones as Activators of Palladium(II) Precatalysts in Amine Arylation Reactions
journal contributionposted on 17.03.2020, 21:29 by Huaiyuan Hu, Ashley M. Gilliam, Fengrui Qu, Kevin H. Shaughnessy
Enolizable ketones have been identified as effective activators for palladium(II) precatalysts in the coupling of aryl bromides and aniline. N-arylation reactions catalyzed by [(DTBNpP)PdCl2]2 (DTBNpP = (bis(tert-butyl)neopentylphosphine) and PEPPSI-IPr precatalysts are activated by the addition of acetone, mesityl oxide, and 3-pentanone. 3-Pentanone was the most effective activator. Mechanistic studies show that acetone, 3-pentanone, and mesityl oxide reduce [(DTBNpP)PdCl2]2 in the presence of NaO-t-Bu to Pd0(DTBNpP)2.