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-1<i>H</i>-benzo[<i>e</i>][1,4]diazepin-5(2<i>H</i>)-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 (CO<sub>2</sub>R) group has a strong <i>ortho</i>-substituent effect on a Goldberg-type C–N coupling reaction.

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