Copper Nanoparticles in Click Chemistry

Accounts of Chemical Research

Volumn 48, Issue 9, 2015, Pages 2516-2528

  Alonso, Francisco ^a   Moglie, Yanina ^b   Radivoy, Gabriel ^b  

^a UNIVERSITY OF ALICANTE   (Spain)

^b UNIVERSIDAD NACIONAL DEL SUR   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84941670893     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.5b00293     Document Type: Article

References (77)

1. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions Angew. Chem., Int. Ed. 2001, 40, 2004-2021 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5
2. Tornøe, C. W.; Meldal, M. Peptidotriazoles: Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions on Solid-Phase. In The Wave of the Future; Lebl, M.; Houghten, R. A., Eds.; American Peptide Society and Kluwer Academic Publishers: San Diego, 2001; pp 263-264.
3. Tornøe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides J. Org. Chem. 2002, 67, 3057-3064 10.1021/jo011148j
4. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective ′Ligation′' of Azides and Terminal Alkynes Angew. Chem., Int. Ed. 2002, 41, 2596-2599 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
5. Huisgen, R.; Knorr, R.; Möbius, L.; Szeimies, G. 1.3-Dipolare Cycloadditionen, XXIII. Einige Beobachtungen zur Addition Organischer Azide an CC-Dreifachbindungen Chem. Ber. 1965, 98, 4014-4021 10.1002/cber.19650981228
6. Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. CuI-Catalyzed Alkyne-Azide ′Click′' Cycloadditions from a Mechanistic and Synthetic Perspective Eur. J. Org. Chem. 2006, 51-68 10.1002/ejoc.200500483
7. Meldal, M.; Tornøe, C. W. Cu-Catalyzed Azide-Alkyne Cycloaddition Chem. Rev. 2008, 108, 2952-3015 10.1021/cr0783479
8. Fokin, V. V. CuAAC: The Quintessential Click Reaction. In Organic Chemistry'-'Breakthroughs and Perspectives, 1 st ed.; Ding, K.; Dai, L.-X., Eds.; Wiley-VCH: Weinheim, Germany, 2012; Chapter 7, pp 247-277.
9. Wang, Q.; Hawker, C. Toward a Few Good Reactions: Celebrating Click Chemistry′'s First Decade Chem.-Asian J. 2011, 6, 2568-2569 10.1002/asia.201100755
10. For a special issue, see: Chem.-Asian J. 2011, 6, 2565-2847.
11. Click Chemistry for Biotechnology and Materials Science; Lahann, J., Ed.; Wiley: Chichester, U.K., 2009.
12. Thirumurugan, P.; Matosiuk, D.; Jozwiak, K. Click Chemistry for Drug Development and Diverse Chemical-Biology Applications Chem. Rev. 2013, 113, 4905-4979 10.1021/cr200409f
13. Anastas, P.; Eghbali, N. Green Chemistry: Principles and Practice Chem. Soc. Rev. 2010, 39, 301-312 10.1039/B918763B
14. Nanoparticles and Catalysis; Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany, 2008.
15. Selective Nanocatalysts and Nanoscience, 1 st ed.; Zecchina, A.; Bordiga, S.; Groppo, E., Eds.; Wiley-VCH: Weinheim, Germany, 2011.
16. Nanomaterials in Catalysis; Serp, P.; Philippot, K., Eds.; Wiley-VCH: Weinheim, Germany, 2013.
17. For a special issue, see: Nanoparticles for Catalysis. Acc. Chem. Res. 2013, 46, 1671-1910.
18. Metal Nanoparticles for Catalysis: Advances and Applications; Tao, F., Ed.; Royal Society of Chemistry: Cambridge, U.K., 2014.
19. For a review, see: Campelo, J. M.; Luna, D.; Luque, R.; Marinas, J. M.; Romero, A. A. Sustainable Preparation of Supported Metal Nanoparticles and their Applications in Catalysis ChemSusChem 2009, 2, 18-45 10.1002/cssc.200800227
20. Nasir Baig, R. B.; Varma, R. S. Nanocatalysis in Water. In Metal-Catalyzed Reactions in Water; Dixneuf, P. H.; Cadierno, V., Eds.; Wiley-VCH: Weinheim, Germany, 2013; Chapter 9, pp 337-394.
21. Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. Copper(I)-Catalyzed Synthesis of Azoles. DFT Study Predicts Unprecedented Reactivity and Intermediates J. Am. Chem. Soc. 2005, 127, 210-216 10.1021/ja0471525
22. Gommermann, N.; Gehrig, A.; Knochel, P. Enantioselective Synthesis of Chiral α-Aminoalkyl-1,2,3-triazoles Using a Three-Component Reaction Synlett 2005, 2796-2798 10.1055/s-2005-918931
23. Jin, T.; Yan, M.; Yamamoto, Y. Click Chemistry of Alkyne-Azide Cycloaddition Using Nanostructured Copper Catalysts ChemCatChem 2012, 4, 1217-1229 10.1002/cctc.201200193
24. Woo, H.; Kang, H.; Kim, A.; Jang, S.; Park, J. C.; Park, S.; Kim, B.-S.; Song, H.; Park, K. H. Azide-Alkyne Huisgen [3 + 2] Cycloaddition Using CuO Nanoparticles Molecules 2012, 17, 13235-13252 10.3390/molecules171113235
25. For the first applications of finally divided metals in organic chemistry, see: Sabatier, P. La Catalyse en Chimie Organique; Librairie Polytechnique Ch.Béranger: Paris, 1913.
26. Rieke, R. D. Use of Activated Metals in Organic and Organometallic Synthesis Top. Curr. Chem. 1975, 59, 1-31 10.1007/BFb0046185
27. Fürstner, A. Active Metals; Wiley-VCH: Weinheim, Germany, 1996.
28. Alonso, F.; Vitale, C.; Radivoy, G.; Yus, M. Reduction of Carbonyl Compounds and Imines using the CuCl2·2H2O-Li-DTBB(cat.) Combination Synthesis 2003, 443-447 10.1055/s-2003-37357
29. Alonso, F.; Moglie, Y.; Radivoy, G.; Vitale, C.; Yus, M. Hydrodehalogenation of Organic Halides using the CuCl2·2H2O-Li-arene(cat.) Combination Appl. Catal., A 2004, 271, 171-176 10.1016/j.apcata.2004.01.038
30. Radivoy, G.; Alonso, F.; Moglie, Y.; Vitale, C.; Yus, M. Reduction of Alkyl and Vinyl Sulfonates Using the CuCl2·2H2O-Li-DTBB(cat.) System Tetrahedron 2005, 61, 3859-3864 10.1016/j.tet.2005.01.078
31. Berg, R.; Straub, J.; Schreiner, E.; Mader, S.; Rominger, F.; Straub, B. F. Highly Active Dinuclear Copper Catalysts for Homogeneous Azide-Alkyne Cycloadditions Adv. Synth. Catal. 2012, 354, 3445-3450 10.1002/adsc.201200734
32. Deraedt, C.; Pinaud, N.; Astruc, D. Recyclable Catalytic Dendrimer Nanoreactor for Part-Per-Million CuI Catalysis of ′Click′' Chemistry in Water J. Am. Chem. Soc. 2014, 136, 12092-12098 10.1021/ja5061388
33. Durán Pachón, L.; van Maarseveen, J. H.; Rothenberg, G. Click Chemistry: Copper Clusters Catalyse the Cycloaddition of Azides with Terminal Alkynes Adv. Synth. Catal. 2005, 347, 811-815 10.1002/adsc.200404383
34. Orgueira, H. A.; Fokas, D.; Isome, Y.; Chan, P. C.-M.; Baldino, C. M. Regioselective Synthesis of [1,2,3]-Triazoles Catalyzed by Cu(I) Generated in situ from Cu(0) Nanosize Activated Powder and Amine Hydrochloride Salts Tetrahedron Lett. 2005, 46, 2911-2914 10.1016/j.tetlet.2005.02.127
35. Molteni, G.; Bianchi, C. L.; Marinoni, G.; Santo, N.; Ponti, A. Cu/Cu-Oxide Nanoparticles as Catalyst in the ′Click′' Azide-Alkyne Cycloaddition New J. Chem. 2006, 30, 1137-1139 10.1039/b604297j
36. Sarkar, A.; Mukherjee, T.; Kapoor, S. PVP-Stabilized Copper Nanoparticles: A Reusable Catalyst for ′Click′' Reaction between Terminal Alkynes and Azides in Nonaqueous Solvents J. Phys. Chem. C 2008, 112, 3334-3340 10.1021/jp077603i
37. Astruc, D.; Lu, F.; Ruiz Aranzaes, J. Nanoparticles as Recyclable Catalysts: The Frontier between Homogeneous and Heterogeneous Catalysis Angew. Chem., Int. Ed. 2005, 44, 7852-7872 10.1002/anie.200500766
38. Franke, R.; Rothe, J.; Pollmann, J.; Hormes, J.; Bönnemann, H.; Brijoux, W.; Hindenburg, T. A Study of the Electronic and Geometric Structure of Colloidal Ti0·0.5THF J. Am. Chem. Soc. 1996, 118, 12090-12097 10.1021/ja953525d
39. Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Copper Nanoparticles in Click Chemistry: an Alternative Catalytic System for the Cycloaddition of Terminal Alkynes and Azides Tetrahedron Lett. 2009, 50, 2358-2362 10.1016/j.tetlet.2009.02.220
40. Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Unsupported Copper Nanoparticles in the 1,3-Dipolar Cycloaddition of Terminal Alkynes and Azides Eur. J. Org. Chem. 2010, 1875-1884 10.1002/ejoc.200901446
41. Pérez-Balderas, F.; Ortega-Mun"oz, M.; Morales-Sanfrutos, J.; Hernández-Mateo, F.; Calvo-Flores, F. G.; Calvo-Asín, J. A.; Isac-García, J.; Santoyo-González, F. Multivalent Neoglycoconjugates by Regiospecific Cycloaddition of Alkynes and Azides Using Organic Soluble Copper Catalysts Org. Lett. 2003, 5, 1951-1954 10.1021/ol034534r
42. Hein, J. E.; Fokin, V. V. Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) and Beyond: New Reactivity of Copper(I) Acetylides Chem. Soc. Rev. 2010, 39, 1302-1315 10.1039/b904091a
43. Buckley, B. R.; Heaney, H. Mechanistic Investigations of Copper(I)-Catalysed Alkyne-Azide Cycloaddition Reactions Top. Heterocycl. Chem. 2012, 28, 1-30 10.1007/7081
44. Nolte, C.; Mayer, P.; Straub, B. F. Isolation of a Copper(I) Triazolide: A ′Click′' Intermediate Angew. Chem., Int. Ed. 2007, 46, 2101-2103 10.1002/anie.200604444
45. Straub, B. F. Acetylide and Alkenylidene Ligands in ′Click′' Triazole Syntheses Chem. Commun. 2007, 3868-3870 10.1039/b706926j
46. Ahlquist, M.; Fokin, V. V. Enhanced Reactivity of Dinuclear Copper(I) Acetylides in Dipolar Cycloadditions Organometallics 2007, 26, 4389-4391 10.1021/om700669v
47. Buckley, B. R.; Dann, S. E.; Heaney, H. Experimental Evidence for the Involvement of Dinuclear Alkynylcopper(I) Complexes in Alkyne-Azide Chemistry Chem.-Eur. J. 2010, 16, 6278-6284 10.1002/chem.201000447
48. Worrell, B. T.; Malik, J. A.; Fokin, V. V. Direct Evidence of a Dinuclear Copper Intermediate in Cu(I)-Catalyzed Azide-Alkyne Cycloadditions Science 2013, 340, 457-460 10.1126/science.1229506
49. Lipshutz, B. H.; Taft, B. R. Heterogeneous Copper-in-Charcoal-Catalyzed Click Chemistry Angew. Chem., Int. Ed. 2006, 45, 8235-8238 10.1002/anie.200603726
50. Chassaing, S.; Sido, A. S. S.; Alix, A.; Kumarraja, M.; Pale, P.; Sommer, J. ′Click Chemistry′' in Zeolites: Copper(I) Zeolites as New Heterogeneous and Ligand-Free Catalysts for the Huisgen [3 + 2] Cycloaddition Chem.-Eur. J. 2008, 14, 6713-6721 10.1002/chem.200800479
51. Sirion, U.; Bae, Y. J.; Lee, B. S.; Chi, D. Y. Ionic Polymer Supported Copper(I): A Reusable Catalyst for Huisgen′'s 1,3-Dipolar Cycloaddition Synlett 2008, 2326-2330 10.1055/s-2008-1078245
52. Park, I. S.; Kwon, M. S.; Kim, Y.; Lee, J. S.; Park, J. Heterogeneous Copper Catalyst for the Cycloaddition of Azides and Alkynes without Additives under Ambient Conditions Org. Lett. 2008, 10, 497-500 10.1021/ol702790w
53. Smith, C. D.; Baxendale, I. R.; Lanners, S.; Hayward, J. J.; Smith, S. C.; Ley, S. V. [3 + 2] Cycloaddition of Acetylenes with Azides to Give 1,4-Disubstituted 1,2,3-Triazoles in a Modular Flow Reactor Org. Biomol. Chem. 2007, 5, 1559-1561 10.1039/b702995k
54. For a minireview of heterogeneous AAC, see: Dervaux, B.; Du Prez, F. E. Chem. Sci. 2012, 3, 959-966 10.1039/C2SC00848C
55. Feldman, A. K.; Colasson, B.; Fokin, V. V. One-Pot Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from In Situ Generated Azides Org. Lett. 2004, 6, 3897-3899 10.1021/ol048859z
56. Appukkuttan, P.; Dehaen, W.; Fokin, V. V.; Van der Eycken, E. A Microwave-Assisted Click Chemistry Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via a Copper(I)-Catalyzed Three-Component Reaction Org. Lett. 2004, 6, 4223-4225 10.1021/ol048341v
57. Miao, T.; Wang, L. Regioselective Synthesis of 1,2,3-Triazoles by Use of Silica-Supported Copper(I) Catalyst Synthesis 2008, 363-368 10.1055/s-2008-1032037
58. Bénéteau, V.; Olmos, A.; Boningari, T.; Sommer, J.; Pale, P. Zeo-Click Synthesis: CuI-Zeolite-Catalyzed One-Pot Two-Step Synthesis of Triazoles from Halides and Related Compounds Tetrahedron Lett. 2010, 51, 3673-3677 10.1016/j.tetlet.2010.05.036
59. Laksmi Kantam, M.; Swarna Jaya, V.; Sreedhar, B.; Mohan Rao, M.; Choudary, B. M. Preparation of Alumina Supported Copper Nanoparticles and their Application in the Synthesis of 1,2,3-Triazoles J. Mol. Catal. A: Chem. 2006, 256, 273-277 10.1016/j.molcata.2006.04.054
60. Sharghi, H.; Khalifeh, R.; Doroodmand, M. M. 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 Adv. Synth. Catal. 2009, 351, 207-218 10.1002/adsc.200800612
61. Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Multicomponent Synthesis of 1,2,3-Triazoles in Water Catalysed by Copper Nanoparticles on Activated Carbon Adv. Synth. Catal. 2010, 352, 3208-3214 10.1002/adsc.201000637
62. Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Click Chemistry from Organic Halides, Diazonium Salts and Anilines in Water Catalysed by Copper Nanoparticles on Activated Carbon Org. Biomol. Chem. 2011, 9, 6385-6395 10.1039/c1ob05735a
63. Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Multicomponent Click Synthesis of Potentially Biologically Active Triazoles Catalysed by Copper Nanoparticles on Activated Carbon in Water Heterocycles 2012, 84, 1033-1044 10.3987/COM-11-S(P)81
64. Decan, M. R.; Impellizzeri, S.; Marin, M. L.; Scaiano, J. C. Copper Nanoparticle Heterogeneous Catalytic ′Click′' Cycloaddition Confirmed by Single-Molecule Spectroscopy Nat. Commun. 2014, 5, 4612 10.1038/ncomms5612
65. Nador, F.; Volpe, M. A.; Alonso, F.; Feldhoff, A.; Kirschning, A.; Radivoy, G. Copper Nanoparticles Supported on Silica Coated Maghemite as Versatile, Magnetically Recoverable and Reusable Catalyst for Alkyne Coupling and Cycloaddition Reactions Appl. Catal., A 2013, 455, 39-45 10.1016/j.apcata.2013.01.023
66. Barral, K.; Moorhouse, A. D.; Moses, J. E. Efficient Conversion of Aromatic Amines into Azides: A One-Pot Synthesis of Triazole Linkages Org. Lett. 2007, 9, 1809-1811 10.1021/ol070527h
67. Moorhouse, A. D.; Moses, J. E. Microwave Enhancement of a ′'One-Pot′' Tandem Azidation-′'Click′' Cycloaddition of Anilines Synlett 2008, 2089-2092 10.1055/s-2008-1078019
68. Amantini, D.; Fringuelli, F.; Piermatti, O.; Tortoioli, S.; Vaccaro, L. Nucleophilic Ring Opening of 1,2-Epoxides in Aqueous Medium ARKIVOC 2002, xi) 293-311
69. Yadav, J. S.; Subba Reddy, B. V.; Madhusudhan Reddy, G.; Narasimha Chary, D. Three Component, Regioselective, One-Pot Synthesis of β-Hydroxytriazoles from Epoxides via ′'Click Reactions′' Tetrahedron Lett. 2007, 48, 8773-8776 10.1016/j.tetlet.2007.09.160
70. Kumaraswamy, G.; Ankamma, K.; Pitchaiah, A. Tandem Epoxide or Aziridine Ring Opening by Azide/Copper Catalyzed [3 + 2] Cycloaddition: Efficient Synthesis of 1,2,3-Triazolo β-Hydroxy or β-Tosylamino Functionality Motif J. Org. Chem. 2007, 72, 9822-9825 10.1021/jo701724f
71. Rajender Reddy, K.; Uma Maheswari, C.; Rajgopal, K.; Lakshmi Kantam, M. One-Pot Sequential Synthesis of β-Hydroxy-1,4-disubstituted-1,2,3-triazoles from In-Situ Generated β-Azido Alcohol by Click Chemistry Synth. Commun. 2008, 38, 2158-2167 10.1080/00397910802026329
72. Sharghi, H.; Beyzavi, M. H.; Safavi, A.; Doroodmand, M. M.; Khalifeh, R. Immobilization of Porphyrinatocopper Nanoparticles onto Activated Multi-Walled Carbon Nanotubes and a Study of its Catalytic Activity as an Efficient Heterogeneous Catalyst for a Click Approach to the Three-Component Synthesis of 1,2,3-Triazoles in Water Adv. Synth. Catal. 2009, 351, 2391-2410 10.1002/adsc.200900353
73. Sharghi, H.; Hosseini-Sarvari, M.; Moeini, F.; Khalifeh, R.; Beni, A. S. One-Pot, Three-Component Synthesis of 1-(2-Hydroxyethyl)-1H-1,2,3-Triazole Derivatives by Copper-Catalyzed 1,3-Dipolar Cycloaddition of 2-Azido Alcohols and Terminal Alkynes under Mild Conditions in Water Helv. Chim. Acta 2010, 93, 435-449 10.1002/hlca.200900226
74. Boningari, T.; Olmos, A.; Reddy, B. M.; Sommer, J.; Pale, P. Zeo-Click Chemistry: Copper(I)-Zeolite-Catalyzed Cascade Reaction; One-Pot Epoxide Ring-Opening and Cycloaddition Eur. J. Org. Chem. 2010, 6338-6347 10.1002/ejoc.201000802
75. Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Multicomponent Click Synthesis of 1,2,3-Triazoles from Epoxides in Water Catalyzed by Copper Nanoparticles on Activated Carbon J. Org. Chem. 2011, 76, 8394-8405 10.1021/jo2016339
76. Trost, B. M.; Shibata, T. Nucleophilic Attack on Olefins Initiated by Dimethyl(methylthio)sulfonium Fluoroborate (DMTSF). Azasulfenylation J. Am. Chem. Soc. 1982, 104, 3225-3228 10.1021/ja00375a054
77. Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Alkenes as Azido Precursors for the One-Pot Synthesis of 1,2,3-Triazoles Catalyzed by Copper Nanoparticles on Activated Carbon J. Org. Chem. 2013, 78, 5031-5037 10.1021/jo400110m