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An unusual cyclometallation reaction at palladium is described, which proceeds via C–H functionalisation of a vinylic C(sp2)–H bond tethered to an NHC ligand. The energetic balance between palladacycle formation and bis-NHC complexation has been found to be very subtle.

Graphical abstract: σ-Alkenyl endo-palladacycle formation via regiospecific functionalisation of an unreactive NHC-tethered C(sp2)–H bond

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