Palladium-catalyzed cross-coupling of heterocyclic silanolates with aryl halides

ORGN 633

Scott E. Denmark, denmark@scs.uiuc.edu and John D. Baird, jdb@scs.uiuc.edu. Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, IL 61801
A variety of heterocyclic sodium silanolates prepared by stoichiometric deprotonation undergo palladium-catalyzed cross-coupling with substituted aryl iodides and bromides. Silanolates prepared from indole, pyrrole, furan and thiophene are stable, easily handled reagents for cross-coupling. Key variables that led to successful cross-coupling include solvent, catalyst, and additive. The substituted heterocyclic products are obtained in good yields under mild conditions.