190314-15-9Relevant articles and documents
Palladium-catalyzed condensation of N -aryl imines and alkynylbenziodoxolones to form multisubstituted furans
Lu, Beili,Wu, Junliang,Yoshikai, Naohiko
supporting information, p. 11598 - 11601 (2014/10/16)
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.