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A novel, electron-deficient cyclopentadienyl iridium(III) catalyst enables sequential cleavage of arene C(sp 2 )-H and methoxy C(sp 3 )-H bonds of anisoles, generating reactive metalacycles that insert difluoroalkynes to afford chromenes under mild reaction conditions. This transformation is an arylalkylation of an alkyne-a carbocarbation-via a nonchelate-assisted cleavage of two C-H bonds.

Ir(III)-Catalyzed Carbocarbation of Alkynes through Undirected Double C–H Bond Activation of Anisoles