title: Resin-supported catalysts for CuAAC click reactions in aqueous or organic solvents.
abstract: The copper-catalyzed azide-alkyne cycloaddition click reaction is a valuable process for the synthesis of libraries of drug candidates, derivatized polymers and materials, and a wide variety of other functional molecules. In some circumstances, the removal of the copper catalyst is both necessary and inconvenient. We describe here two immobilized forms of a Cu-binding ligand that has been shown to accelerate triazole formation under many different conditions, using different resin supports that are appropriate for aqueous or organic solvents. Copper leaching from these resins was modest, allowing them to be reused in many reaction/filtration cycles without recharging with metal ion. The utility of this catalyst form was demonstrated in the convenient synthesis of 20 N-acetylgalactosamine derivatives for biological testing.
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Stanislav I
authors.initials: SI
authors.lastname: Presolski
authors.forename: Sreeman K
authors.initials: SK
authors.lastname: Mamidyala
authors.forename: Florian
authors.initials: F
authors.lastname: Manzenrieder
authors.forename: M G
authors.initials: MG
authors.lastname: Finn
mesh_terms: D000117:Acetylglucosamine / Q000138:chemical synthesis / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D008024:Ligands; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012117:Resins, Synthetic / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D014867:Water / Q000737:chemistry
chemical_list: D000480:Alkynes; D001386:Azides; D008024:Ligands; D009942:Organometallic Compounds; D012117:Resins, Synthetic; D012997:Solvents; D014867:Water; D003300:Copper; D000117:Acetylglucosamine