Organic Chemistry Portal

Abstracts

Search:

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: rbateychem.utoronto.ca

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

DOI: 10.1021/ol4013712 (free Supporting Information)


Abstract

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.

see article for more examples



Key Words

Chan-Lam Coupling, Esters, Oxygen


ID: J54-Y2013