The last decades have witnessed a tremendous progress in the field of transition metal-catalyzed C–H functionalization. While the activation and functionalization of aromatic C(sp2)–H bonds has become routine, the functionalization of more challenging alkyl C(sp3)–H bonds has gained momentum only recently, especially with the use of palladium(II) catalytsts. The transition metal-catalyzed oxidative annulation of C(sp3)–H bonds is the most desirable approach for the conversion of readily available raw feedstocks into useful saturated heterocyclic cores, widespread motifs in value-added commodity chemicals. For the past few years our research team has developed a research program on the discovery of formal cycloaddition reactions involving C–H activation pathways. Herein we demonstrate for the first time that palladium(II) catalysts promote the annulation of alkyl amides and dienes to form a great variety of synthetically appealing saturated lactams via C(sp3)–H functionalization pathways. Mechanistic studies, including the isolation and full characterization of an alkyl-PdIIreaction intermediate, reveal that bulky monodentate quinoline ligands and diene partners are key to favor migratory insertion/reductive elimination pathways leading to the formation of the desired cycloadducts over unproductive secondary reactions.

Palladium(II)-Catalyzed Formal (4+2) Cycloaddition between Alkyl Amides and Dienes via C(sp3)–H Activation: Direct Access to the Piperidone Core

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