Palladium-catalyzed condensation of N -aryl imines and alkynylbenziodoxolones to form multisubstituted furans

Beili Lu, Junliang Wu, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

Abstract

A palladium(II) catalyst promotes condensation of an N-aryl imine and an alkynylbenziodoxolone derivative to afford a multisubstituted furan, whose substituents are derived from the alkynyl moiety (2-position), the imine (3- and 4-positions), and the 2-iodobenzoate moiety (5-position), along with an N-arylformamide under mild conditions. The 2-iodophenyl group of the furan product serves as a versatile handle for further transformations. A series of isotope-labeling experiments shed light on the bond reorganization process in this unusual condensation reaction, which includes cleavage of the C-C triple bond and fragmentation of the carboxylate moiety.

Original languageEnglish
Pages (from-to)11598-11601
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number33
DOIs
Publication statusPublished - 2014 Aug 20
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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