title: Modular synthesis of multisubstituted furans through palladium-catalyzed three-component condensation of alkynylbenziodoxoles, carboxylic acids, and imines.
abstract: Mild and regiocontrolled synthesis of a multisubstituted furan is achieved through Pd(OAc)2 -catalyzed room-temperature condensation of an alkynylbenziodoxole, a carboxylic acid, and an enolizable ketimine, which contribute to C1, CO, and C2 fragments, respectively, to the furan skeleton. The reaction tolerates a broad range of functional groups in each of the reaction components, and enables highly modular and flexible synthesis of variously substituted furans. The reaction is particularly effective for the rapid generation of tri- and tetraarylfurans and furan-containing oligoarylenes without relying on conventional cross-coupling chemistry.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore).
authors.forename: Junliang
authors.initials: J
authors.lastname: Wu
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore). nyoshikai@ntu.edu.sg.
authors.forename: Naohiko
authors.initials: N
authors.lastname: Yoshikai
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry*; D007462:Iodobenzenes; D007463:Iodobenzoates / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D005663:Furans; D007097:Imines; D007462:Iodobenzenes; D007463:Iodobenzoates; C476101:o-iodoxybenzoic acid; D010165:Palladium
keywords: furans; hypervalent iodine compounds; imines; multicomponent reactions; palladium