Resin-Supported Catalysts for CuAAC Click Reactions in Aqueous or Organic Solvents

• Published in: ACS combinatorial science Vol. 14; no. 10; pp. 527 - 530
• Main Authors: Presolski, Stanislav I, Mamidyala, Sreeman K, Manzenrieder, Florian, Finn, M.G
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 08.10.2012; Amer Chemical Soc
• Subjects: Acetylglucosamine - chemical synthesis; Acetylglucosamine - chemistry; Alkynes - chemistry; Azides - chemistry; Catalysis; Catalysts; Chemistry; Chemistry, Applied; Chemistry, Medicinal; Chemistry, Multidisciplinary; Click Chemistry; Combinatorial analysis; Copper; Copper - chemistry; Cyclization; Life Sciences & Biomedicine; Ligands; Molecular Structure; Organometallic Compounds - chemistry; Pharmacology & Pharmacy; Physical Sciences; Polymers; Resins; Resins, Synthetic - chemistry; Science & Technology; Solvents; Solvents - chemistry; Synthesis; Water - chemistry; copper catalyst; CuAAC click reactions; resin-supported catalysts; AZIDE-ALKYNE CYCLOADDITION; LIGANDS; EFFICIENT
• ISSN: 2156-8952; 2156-8944; 2156-8944
• DOI: 10.1021/co300076k

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.