Ni-Catalyzed Alkene Carboacylation via Amide C–N Bond Activation

• Published in: Journal of the American Chemical Society Vol. 139; no. 30; pp. 10228 - 10231
• Main Authors: Walker, James A, Vickerman, Kevin L, Humke, Jenna N, Stanley, Levi M
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 02.08.2017; Amer Chemical Soc
• Subjects: amides; catalysts; chemical bonding; Chemistry; Chemistry, Multidisciplinary; esters; nickel; Physical Sciences; Science & Technology; BENZOCYCLOBUTENONES; KETONE SYNTHESIS; NICKEL CATALYSIS; ARYL ESTERS; HETEROCYCLIC CARBENE COMPLEXES; TWISTED AMIDES; OLEFINS; CLEAVAGE; QUATERNARY CENTERS; GENERAL-METHOD

We report Ni-catalyzed formal carboacylation of o-allylbenzamides with arylboronic acid pinacol esters. The reaction is triggered by oxidative addition of an activated amide C–N bond to a Ni(0) catalyst and proceeds via alkene insertion into a Ni­(II)–acyl bond. The exo-selective carboacylation reac...