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A palladium catalytic method has been developed for the coupling of amides and cyclopropanols to γ-diketones, through simultaneous C–N and C–C activation. Heteroatom ligand exchange and heteroatom-to-carbon ligation mode switching enable the achievement of molecular cross-coupling in an amide N-atom structural context-dependent manner, avoiding any stoichiometric organometallic reagent or base. [ABSTRACT FROM AUTHOR]

Appendage speciation-oriented synthesis, as opposed to the conventional wisdom of skeleton speciation-oriented synthesis, is reported herein, emphasizing the maximization of type-, position-, and configuration-variance of appendages. A Co(III) catalytic protocol in accordance with this synthetic modality has been established for the coupling of enaminones and oxadiazolones to imidazoles, allowing the achievement of full position-variance of appendages. This translates to an expanded reaction and structural development scope and can provide fertile ground for productive organic synthesis.