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

…, RH Szumigala, PG Dormer, JD Armstrong…

Index: Gauthier Jr., Donald R.; Szumigala Jr., Ronald H.; Dormer, Peter G.; Armstrong III, Joseph D.; Volante; Reider, Paul J. Organic Letters, 2002 , vol. 4, # 3 p. 375 - 378

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Citation Number: 45

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.