Copper-Catalyzed C–N Cross-Coupling of Substituted 2-Halobenzoates with Secondary Acyclic Amides

Abstract

The copper-catalyzed C–N cross-coupling of poorly nucleophilic acyclic secondary amides with sterically hindered substituted 2-halobenzoates has been demonstrated with 1,4-dimethyl-3,4-dihydro-1H-benzo[e][1,4]diazepin-5(2H)-one (DMBDO) as ligands for the first time. The protocol is effective for the synthesis of hindered tertiary amides. We also found that the alkoxycarbonyl (CO₂R) group has a strong ortho-substituent effect on a Goldberg-type C–N coupling reaction.

Key words

copper - N-arylation - cross-coupling - amides - halobenzoates

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