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Exposure of aromatic carboxamides 1e-1m, heteroaromatic carboxamides 1n-1p, and alpha,beta-unsaturated carboxamides 1q-1s to 1,1-dimethylallene in the presence of the a cationic iridium complex derived from [Ir(cod)(2)]BAr(F)(4) and rac-BINAP results in direct C-H prenylation to furnish adducts 2e-2m, 2n-2p, and 2q-2s, respectively, in good isolated yields as single isomers.

Direct Prenylation of Aromatic and α,β-Unsaturated Carboxamides via Iridium-Catalyzed C−H Oxidative Addition−Allene Insertion