Synthesis of 5-Pyridyl-2-furaldehydes via Palladium-Catalyzed Cross-Coupling with Triorganozincates.
2010
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.
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