Magnetic starch nanocomposite as a green heterogeneous support for immobilization of large amounts of copper ions: heterogeneous catalyst for click synthesis of 1,2,3-triazoles

A new magnetic heterogeneous copper catalyst was prepared by immobilization of copper ions onto a cross-linked polymeric nanocomposite composed of starch grafted polyacrylamide and functionalized Fe3O4 magnetic nanoparticles. The resulting support was loaded with large amounts of copper ions (1.6 mmol g−1). The prepared catalyst is highly active in Huisgen 1,3-dipolar cycloaddition reactions of different azides and alkynes at low catalyst amounts. Various corresponding 1,2,3-triazoles were produced with high yields in mild conditions. The catalyst was easily recovered and reused for ten cycles of reaction and no significant loss of catalytic activity was observed.

[1]  P. Szafrański,et al.  A new water-soluble ligand for efficient copper-catalyzed Huisgen cycloaddition of aliphatic azides and alkynes , 2015 .

[2]  V. Fernandez,et al.  Graphite-supported ultra-small copper nanoparticles – Preparation, characterization and catalysis applications , 2015 .

[3]  Estela Haldón,et al.  Copper-catalysed azide-alkyne cycloadditions (CuAAC): an update. , 2015, Organic & biomolecular chemistry.

[4]  L. Saikia,et al.  Magnetically recoverable chitosan-stabilised copper–iron oxide nanocomposite material as an efficient heterogeneous catalyst for azide–alkyne cycloaddition reactions , 2015 .

[5]  Shaibal Banerjee,et al.  PVP coated copper–iron oxide nanocomposite as an efficient catalyst for Click reactions , 2015 .

[6]  R. Islam,et al.  Microwave assisted azide–alkyne cycloaddition reaction using polymer supported Cu(I) as a catalytic species: a solventless approach , 2015 .

[7]  A. Pourjavadi,et al.  Copper loaded cross-linked poly(ionic liquid): robust heterogeneous catalyst in ppm amount , 2015 .

[8]  A. Pourjavadi,et al.  Magnetic nanoparticles entrapped in the cross-linked poly(imidazole/imidazolium) immobilized Cu(II): an effective heterogeneous copper catalyst , 2014 .

[9]  P. Wadgaonkar,et al.  Cellulose supported cuprous iodide nanoparticles (Cell-CuI NPs): a new heterogeneous and recyclable catalyst for the one pot synthesis of 1,4-disubstituted – 1,2,3-triazoles in water , 2014 .

[10]  Weixian Xi,et al.  Click Chemistry in Materials Science , 2014 .

[11]  Diego Alves,et al.  Recoverable Cu/SiO2 composite-catalysed click synthesis of 1,2,3-triazoles in water media , 2014 .

[12]  K. Ulbrich,et al.  Click chemistry as a powerful and chemoselective tool for the attachment of targeting ligands to polymer drug carriers , 2014 .

[13]  Susmita Roy,et al.  Polymer anchored Cu(II) complex: an efficient and recyclable catalytic system for the one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles starting from anilines in water , 2013 .

[14]  R. Varma,et al.  Copper on chitosan: a recyclable heterogeneous catalyst for azide–alkyne cycloaddition reactions in water , 2013 .

[15]  Xiao-Jing Shi,et al.  Design and synthesis of novel 1,2,3-triazole-dithiocarbamate hybrids as potential anticancer agents. , 2013, European journal of medicinal chemistry.

[16]  Dariusz Matosiuk,et al.  Click chemistry for drug development and diverse chemical-biology applications. , 2013, Chemical reviews.

[17]  B. Ranu,et al.  Solvent-free one-pot synthesis of 1,2,3-triazole derivatives by the ‘Click’ reaction of alkyl halides or aryl boronic acids, sodium azide and terminal alkynes over a Cu/Al2O3 surface under ball-milling , 2013 .

[18]  F. D. Prez,et al.  Heterogeneous azide–alkyne click chemistry: towards metal-free end products , 2012 .

[19]  K. Hara,et al.  Hydroxyapatite-supported copper(II)-catalyzed azide–alkyne [3+2] cycloaddition with neither reducing agents nor bases in water , 2011 .

[20]  K. Lu,et al.  Highly dispersed silica-supported nanocopper as an efficient heterogeneous catalyst : application in the synthesis of 1,2,3-triazoles and thioethers , 2011 .

[21]  O. Reiser,et al.  A copper(I) isonitrile complex as a heterogeneous catalyst for azide-alkyne cycloaddition in water. , 2011, Organic letters.

[22]  M. Yus,et al.  Multicomponent Synthesis of 1,2,3‐Triazoles in Water Catalyzed by Copper Nanoparticles on Activated Carbon , 2010 .

[23]  Allen F. Brooks,et al.  A short, concise synthesis of queuine , 2010 .

[24]  S. Paul,et al.  Silica Functionalized Cu(I) as a Green and Recyclable Heterogeneous Catalyst for the Huisgen 1,3-Dipolar Cycloaddition in Water at Room Temperature , 2010 .

[25]  Lei Zhu,et al.  Apparent copper(II)-accelerated azide-alkyne cycloaddition. , 2009, Organic letters.

[26]  C. R. Becer,et al.  Click chemistry beyond metal-catalyzed cycloaddition. , 2009, Angewandte Chemie.

[27]  Morten Meldal,et al.  Cu-catalyzed azide-alkyne cycloaddition. , 2008, Chemical reviews.

[28]  Giovanni Sorba,et al.  Click chemistry reactions in medicinal chemistry: Applications of the 1,3‐dipolar cycloaddition between azides and alkynes , 2008, Medicinal research reviews.

[29]  K. Rajender Reddy,et al.  Copper-alginates: a biopolymer supported Cu(II) catalyst for 1,3-dipolar cycloaddition of alkynes with azides and oxidative coupling of 2-naphthols and phenols in water , 2007 .

[30]  J. Sommer,et al.  Click chemistry in CuI-zeolites: the Huisgen [3 + 2]-cycloaddition. , 2007, Organic letters.

[31]  Jean-François Lutz,et al.  1,3-dipolar cycloadditions of azides and alkynes: a universal ligation tool in polymer and materials science. , 2007, Angewandte Chemie.

[32]  J. Herscovici,et al.  Reusable polymer-supported catalyst for the [3+2] Huisgen cycloaddition in automation protocols. , 2006, Organic letters.

[33]  M. G. Finn,et al.  Click Chemistry: Diverse Chemical Function from a Few Good Reactions. , 2001, Angewandte Chemie.

[34]  R. Huisgen Kinetics and reaction mechanisms: selected examples from the experience of forty years , 1989 .

[35]  R. Huisgen 1,3-Dipolar Cycloadditions. Past and Future† , 1963 .

[36]  F. Moghaddam,et al.  Copper immobilized onto a triazole functionalized magnetic nanoparticle: a robust magnetically recoverable catalyst for “click” reactions , 2015 .