Pd-catalyzed ortho-arylation of phenylacetamides, benzamides, and anilides with simple arenes using sodium persulfate

Abstract

We report a mild and efficient Pd-catalyzed ortho-arylation of phenylacetamides, benzamides, and anilides with a range of simple arenes using sodium persulfate (Na2S2O8). This green strategy generates biaryl C–C bonds from two unactivated sp2 hybridized C–H bonds. Electron-rich and electron-neutral arenes underwent oxidative arylation under our optimized reaction conditions. In substrates bearing two reactive ortho C–H bonds, selective diarylation via quadruple C–H bond functionalization was possible. The same reaction conditions were extended to an intramolecular cross-coupling for preparing lactams. The synthesis of relevant trifluoroacetate-bridged bimetallic Pd complexes derived from anilides and their stoichiometric reactivity were investigated.