Palladium-catalyzed arylation/heteroarylation of aryl halide-tethered alkenes with propargylic pyridines has been established, which provides direct and efficient access to various oxindole, azaoxindole, dihydrobenzopyran, indole, and benzofuran-linked indolizines in good yields with a broad substrate scope and high functional group tolerance. This process enables the formation of one C-N and two C-C bonds in a single operation through an intramolecular carbopalladation and cycloisomerization sequence. Furthermore, an indolizinone-linked bisheterocyclic framework containing indole and benzofuran could be synthesized conveniently from tertiary propargylic alcohols involving methyl or phenyl migration.
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