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A Synthesis of 3,4-Dihydroisoquinolin-1(2H)-one via the Rhodium-Catalyzed Alkylation of Aromatic Amides with N‑Vinylphthalimide

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journal contribution
posted on 04.10.2018, 00:00 by Qiyuan He, Naoto Chatani
The alkylation of C–H bonds with N-vinylphthalimide by a rhodium-catalyzed reaction of aromatic amides containing an 8-aminoquinoline moiety as the directing group is reported. N-Vinylphthalimide functions as a 2-aminoethylating reagent. The resulting alkylated products can be converted into 3,4-dihydroisoquinolin-1­(2H)-one derivatives in a one-pot transformation. Deuterium-labeling experiments suggest that the reaction proceeds through a carbene mechanism.