title: An efficient continuous flow approach to furnish furan-based biaryls.
abstract: Suzuki cross-couplings of 5-formyl-2-furanylboronic acid with activated or neutral aryl bromides were performed under continuous flow conditions in the presence of (Bu)4N(+)F(-) and the immobilised t-butyl based palladium catalyst CatCart™ FC1032™. Deactivated aryl bromides and activated aryl chlorides were cross-coupled with 5-formyl-2-furanylboronic in the presence of (Bu)4N(+)OAc(-) using the bis-triphenylphosphine CatCart™ PdCl2(PPh3)2-DVB. Initial evidence indicates the latter method may serve as a universal approach to conduct Suzuki cross-couplings with the protocol successfully employed in the synthesis of the current gold standard Hedgehog pathway inhibitor LDE225.
authors.affiliation: Chemistry, Centre for Chemical Biology, The University of Newcastle, University Drive, Callaghan, NSW 2308, Australia. Adam.McCluskey@newcastle.edu.au.
authors.forename: Trieu N
authors.initials: TN
authors.lastname: Trinh
authors.forename: Lacey
authors.initials: L
authors.lastname: Hizartzidis
authors.forename: Andrew J S
authors.initials: AJ
authors.lastname: Lin
authors.forename: David G
authors.initials: DG
authors.lastname: Harman
authors.forename: Adam
authors.initials: A
authors.lastname: McCluskey
authors.forename: Christopher P
authors.initials: CP
authors.lastname: Gordon
mesh_terms: D001713:Biphenyl Compounds / Q000138:chemical synthesis*; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry; D001965:Bromides / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D010165:Palladium / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis*
chemical_list: D001713:Biphenyl Compounds; D001897:Boronic Acids; D001965:Bromides; D005663:Furans; D011725:Pyridines; C561435:sonidegib; D010165:Palladium; C008756:palladium chloride; C039281:furan