Copper-catalyzed C-N cross-coupling of substituted 2-halobenzoates with secondary acyclic amides

Article abstract of DOI:10.1055/s-0033-1338800

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. Georg Thieme Verlag Stuttgart. New York.