Dual Role of Acetanilides: Traceless Removal of a Directing Group through Deacetylation/Diazotation and Palladium-Catalyzed C–C-Coupling Reactions

The acetamide group enables regioselective oxidative ortho-C–H activation reactions, such as Pd-catalyzed acylation. The synthetic utility of these transformations can be significantly enhanced by using the acetamide as a quasi-leaving group in a subsequent conventional Pd-catalyzed coupling or cross-coupling reaction. The concept is illustrated herein for the synthesis of o-alkenyl- and o-arylphenones, which have potential for the synthesis of arylated aromatic heterocycles.