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

Qiyuan He, Naoto Chatani

J Org Chem. 2018 Nov 2;83(21):13587-13594.

PMID: 30284828

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP3485845 N-Vinylphthalimide N-Vinylphthalimide 3485-84-5 Price
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