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Copper-Catalyzed Nondecarboxylative Cross Coupling of Alkenyltrifluoroborate Salts with Carboxylic Acids or Carboxylates: Synthesis of Enol Esters

Fang Huang, Tan D. Quach and Robert A. Batey*

*Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada, Email:

F. Huang, T. D. Quach, R. A. Batey, Org. Lett., 2013, 15, 3058-3061.

DOI: 10.1021/ol4013712


A mild copper-catalyzed Chan-Lam-Evans type cross-coupling reaction enables a stereospecific and regioselective preparation of enol esters from carboxylate salts or carboxylic acids and potassium alkenyltrifluoroborate salts in the presence of oxygen, catalytic CuBr, DMAP and 4 molecular sieves. Overall, this method demonstrates carboxylic acids as suitable reaction partners for nondecarboxylative copper-catalyzed cross-couplings.

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Key Words

Chan-Lam Coupling, Esters, Oxygen

ID: J54-Y2013