Design and synthesis of palladium (II) OCO pincer type complexes and their catalytic role towards the α-arylation of ketones

Twelve OCO bisacetamide ligands 4aa-4dc were synthesized after condensation of isophenylenediamines 1a-1d and anhydride/acyl chlorides. The corresponding Pd(II)-OCO-H (5aa-5ac), Pd(II)-OCO-Me(5ba-5bc), Pd(H)-OCO-OMe(5ca-5cc), Pd(H)-OCO-NO2(5da-5dc) pincer complexes were prepared via C-H activation of precursors and Pd(OAc)(2), and characterized by IR, H-1 NMR, C-13 NMR and elemental analysis. The st-arylation of ketones and aryl bromides catalyzed by 5 under low catalyst loadings (0.1 mol%) show that 5da exhibits the highest catalytic activity, resulting in a 98% isolated yield. (C) 2018 King Saud University. Production and hosting by Elsevier B.V.