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

Research output: Contribution to journalArticle

53 Scopus citations

Abstract

(Equation Presented) 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.

Original languageEnglish (US)
Pages (from-to)375-378
Number of pages4
JournalOrganic Letters
Volume4
Issue number3
DOIs
StatePublished - Feb 7 2002
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Gauthier, D. R., Szumigala, R. H., Dormer, P. G., Armstrong, J. D., Volante, R. P., & Reider, P. J. (2002). Synthesis of 5-Pyridyl-2-furaldehydes via palladium-catalyzed cross-coupling with triorganozincates. Organic Letters, 4(3), 375-378. https://doi.org/10.1021/ol0170612