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An unprecedented C-H alkylation using α,β-unsaturated γ-lactones (butenolides) and dihydrofurans was achieved by the Rh-catalyzed reaction of benzamides. C-C bond formation occurs between the ortho -position of the benzamide derivative and the γ-position of the butenolide or the α-position of the dihydrofuran. The presence of an 8-aminoquinoline directing group is crucial for the success of the reaction. The results of deuterium labeling experiments indicate that the cleavage of the C-H bond is reversible and suggest that a migratory carbene insertion is involved as the key step.

chemical science

Rhodium-catalyzed regioselective addition of the ortho C–H bond in aromatic amides to the C–C double bond in α,β-unsaturated γ-lactones and dihydrofurans