title: Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols.
abstract: The iodocyclization of gem-difluorohomoallenyl and gem-difluorohomopropargyl alcohols with I2 and ICl, respectively, produced the corresponding fluorinated iodofuran analogues in good yields. The iodo substituent in fluorinated 4-iodofurans was utilized as a synthetic handle to prepare multi-substituted 3-fluorofurans using a Suzuki cross-coupling reaction. The yields of both iodocyclization of gem-difluorohomopropargyl alcohol and subsequent Suzuki coupling were dramatically enhanced by microwave irradiation.
authors.affiliation: Department of Chemistry, University of Louisville, Louisville, KY 40292, USA.
authors.forename: Satoru
authors.initials: S
authors.lastname: Arimitsu
authors.forename: Jesse M
authors.initials: JM
authors.lastname: Jacobsen
authors.forename: Gerald B
authors.initials: GB
authors.lastname: Hammond
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D002712:Chlorides; D005663:Furans; D020005:Propanols; D007455:Iodine; C028255:propargyl alcohol