Synthesis of C-6-substituted uridine phosphonates through aerobic ligand-free Suzuki-Miyaura cross-coupling.
An efficient protocol for the construction of C-6-(hetero)aryl-substituted uridine phosphonate analogues utilizing an aerobic, ligand-free Suzuki-Miyaura cross-coupling reaction of a 6-iodo-precursor in aqueous media has been established. The method presents a modular approach toward the target compounds as demonstrated by the synthesis of a small library comprising 14 novel nucleoside phosphonates.
Nencka
Radim
R
Laboratory for Medicinal Chemistry, Faculty of Pharmaceutical Sciences (FFW), Ghent University, Harelbekestraat 72, B-9000, Ghent, Belgium.
Sinnaeve
Davy
D
Karalic
Izet
I
Martins
José C
JC
Van Calenbergh
Serge
S
D000475:Alkenes / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D006865:Hydrogenation; D007202:Indicators and Reagents; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*; D013696:Temperature; D014529:Uridine / Q000138:chemical synthesis* / Q000737:chemistry
D000475:Alkenes; D001897:Boronic Acids; D007202:Indicators and Reagents; D008024:Ligands; D063065:Organophosphonates; D002244:Carbon; D010100:Oxygen; D014529:Uridine