Recyclable clay supported Cu (II) catalyzed tandem one-pot synthesis of 1-aryl-1,2,3-triazoles

• Published in: Tetrahedron Vol. 68; no. 39; pp. 8156 - 8162
• Main Authors: Mohammed, Shabber, Padala, Anil K., Dar, Bashir A., Singh, Baldev, Sreedhar, B., Vishwakarma, Ram A., Bharate, Sandip B.
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 30-09-2012; Elsevier
• Subjects: 1,2,3-Triazoles; Azide-alkyne 1,3-dipolar cycloaddition; Catalysis; CATALYSTS; Catalysts: preparations and properties; Catalytic reactions; Chemistry; Clay (material); CLAYS; Click chemistry; COPPER OXIDE; COPPER SULFATE; Derivatives; Economics; Exact sciences and technology; FABRICATION; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Heterogeneous catalyst; Kinetics and mechanisms; Montmorillonite KSF clay; Nanoparticles; Organic chemistry; PARTICLES; Precursors; Preparations and properties; Reactivity and mechanisms; RECOVERY (WASTES); Synthesis; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; TRIAZOLE; 1,2,3-Triazoles; Azide-alkyne 1,3-dipolar cycloaddition; Heterogeneous catalyst; Montmorillonite KSF clay; Click chemistry; Copper II; One pot reaction; 1,3-Dipolar cycloaddition; Acetylenic compound; Nanoparticle; Copper II Sulfates; 1,2,3-Triazole derivative; Reaction mechanism; Copper I; Aromatic compound; Recycling; Chemical synthesis; Clay; Catalytic reaction; Chemical reagent; Montmorillonite; Regioselectivity; Organic azide; Copper complex; Tandem reaction; Copper Oxides; Azides; Heterogeneous catalysis; Sodium Azides; Arylboronic acid; Boron Organic compounds; Green chemistry; Copper oxide; Boronic acid derivative; Boronic acids; Catalyst; Room temperature; Alkyne
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2012.07.080

Montmorillonite KSF clay supported CuO nanoparticles efficiently catalyzes one-pot aromatic azidonation of aryl boronic acids followed by regioselective azide–alkyne 1,3-dipolar cycloaddition (CuAAC) reaction producing corresponding 1-aryl-1,2,3-triazole derivatives at room temperature in excellent yields without use of any additives. Investigations on mechanism of CuAAC revealed that sodium azide, which is used as azidonating reagent in one-pot protocol reduces Cu(II) to click-active Cu(I). The catalytic efficiency of another Cu(II) source CuSO4 in combination with NaN3 for this one-pot CuAAC protocol, further supported our mechanism. This is the first report for use of Cu(II)/NaN3 catalytic system for CuAAC protocol. The clay–Cu(II) catalyst being ligand-free, leaching-free, easy to synthesize from inexpensive commercially available precursors, recyclable, and environmentally friendly will be highly useful for economical synthesis of 1,4-disubstituted 1,2,3-triazoles.
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