Palladium-Catalyzed Oxidative Nonclassical Heck Reaction of Arylhydrazines with Allylic Alcohols via C-N Bond Cleavage: Access to β-Arylated Carbonyl Compounds.

An efficient palladium-catalyzed oxidative nonclassical Heck reaction of arylhydrazines with allylic alcohols via C-N bond cleavage has been successfully developed. This method provides a series of β-arylated carbonyl compounds with broad functional group tolerance under base-free, simple, and mild open air reaction conditions. In the reaction, arylhydrazines with the smaller molecular weight of the leaving group were employed as the "green" arylation reagent, which released N 2 and water as the byproducts under air. Mechanistic studies suggested that an aryl radical process and Pd-H complex migration reinsertion were involved. Moreover, the synthesis of the antiarrhythmic drug propafenone was completed with this transformation as the key step.