Sulfoximine Aided d-1,1-Cascade Heterocyclization of Unactivated Alkenes

A palladium-catalyzed -annulative 1,1-difunctionalization of unactivated alkene was achieved through the merging of C(alkenyl)H activation and Wacker-type nucleometallation. The 2-pyridyl methyl sulfoximine (MPyS) bidentate directing group in combination with the 2-hydroxy-5-methylpyridine ligand plays a significant in making the transformation viable under mild conditions. The process enables the cascade formation of CC/CN & CC/CO bonds in a single operation, as evidenced by bi-functional reagents (BFRs) from the 2-iodobenzamide, and 2-iodobenzoic acid series. Notably, the de-novo synthesis of -branched isoindolinones/phthalides motifs highlights its practicality. Mechanistic studies uncover the intricacies of the catalytic cycle. Moreover, the ‘N’ to ‘O’ atom swap showcases the skeletal editing of these complex molecular entities; this process provides direct access to the synthesis of monoamine oxidase A inhibitor.