Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols.
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.
Arimitsu
Satoru
S
Department of Chemistry, University of Louisville, Louisville, KY 40292, USA.
Jacobsen
Jesse M
JM
Hammond
Gerald B
GB
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
D000480:Alkynes; D002712:Chlorides; D005663:Furans; D020005:Propanols; D007455:Iodine; C028255:propargyl alcohol