Copper Nanoparticles on Charcoal for Multicomponent Catalytic Synthesis of 1,2,3-Triazole Derivatives from Benzyl Halides or Alkyl Halides, Terminal Alkynes and Sodium Azide in Water as a “Green” Solvent
- ISSN: 16154150
- DOI: 10.1002/adsc.200800612
A one-pot procedure for synthesis of 1,2,3-triazole derivatives via the three-component coupling (TCC) reaction between terminal alkynes, benzyl or alkyl halides, and sodium azide in the presences of 1 mol% nanoparticles copper/carbon (Cu/C) catalyst has been developed. The catalyst showed high catalytic activity and 1,4-regioselectivity for the 3+2 Huisgen cycloaddition in water as a "green" solvent and good to excellent yields were obtained in all cases. This procedure eliminates the need to handle organic azides, and they are generated in situ. The reaction has a broad scope and is especially practical for the synthesis of new azacrown ether and anthraquinone derivatives of triazole. The heterogeneous catalysts were fully characterized by scanning electron microscopy (SEM), atomic forced microscopy (AFM), X-ray diffraction (XRD), inductively coupled plasma (ICP) analysis and FT-IR experimental techniques. The catalyst was recycled ten times without significant loss of activity.