Palladium-catalyzed conversion of alkenes to organoboron compounds

ORGN 549

Nicos A. Petasis, petasis@usc.edu and Kalyan C. Nagulapalli. Department of Chemistry and Loker Hydrocarbon Research Institute, University of Southern California, Los Angeles, CA 90089-1661
Alkyl and alkenyl boronic acids and trifluoroborates are very versatile synthetic intermediates that are widely used in metal-mediated cross-coupling processes, as well as in multicomponent reactions with amines and carbonyls recently developed in our laboratories. The most common methods for the preparation of these organoboron compounds include hydroboration processes or the C-H activation of alkenes catalyzed by iridium or rhodium catalysts. Herein, we report a new and practical method for the synthesis of a number of such organoboron compounds based on a conceptually novel transformation of alkenes catalyzed by palladium. Synthetic and mechanistic aspects of this process will be presented.