Organic Letters 2002-02-07

Synthesis of 5-pyridyl-2-furaldehydes via palladium-catalyzed cross-coupling with triorganozincates.

Donald R Gauthier, Ronald H Szumigala, Peter G Dormer, Joseph D Armstrong, R P Volante, Paul J Reider

Index: Org. Lett. 4(3) , 375-8, (2002)

Full Text: HTML

Abstract

5-Pyridyl- and 5-aryl-2-furaldehydes are prepared from furaldehyde diethyl acetal in a four-step, one-pot procedure:(i) deprotonation; (2) Li to Zn transmetalation; (3) Pd-mediated cross-coupling; (4) aldehyde deprotection. Triorganozincate 7 was found to transfer all three groups in the Pd-catalyzed cross-coupling reaction with haloaromatics.