Amphiphilic self-assembled polymeric copper catalyst to parts per million levels: Click chemistry

Journal of the American Chemical Society

Volumn 134, Issue 22, 2012, Pages 9285-9290

  Yamada, Yoichi M A ^a   Sarkar, Shaheen M ^a   Uozumi, Yasuhiro ^a,b  

^a RIKEN   (Japan)

^b GRADUATE UNIVERSITY FOR ADVANCED STUDIES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,3-DIPOLARCYCLOADDITION; AGGREGATED STRUCTURE; AMPHIPHILICS; CATALYTIC TURNOVER; CLICK CHEMISTRY; COPPER CATALYST; COPPER COMPLEXES; COPPER SULFATE; GLOBULAR PARTICLES; ORGANIC AZIDES; ORGANIC HALIDES; PARTS PER MILLIONS; POLYMERIC LIGANDS; SELF-ASSEMBLED; SODIUM AZIDE; SOLID-PHASE; THREE-COMPONENT;

ACETYLENE; ACRYLIC MONOMERS; AMIDES; CATALYSTS; COPPER; COPPER COMPOUNDS; CYCLOADDITION; HYDROGELS; SODIUM; SYNTHESIS (CHEMICAL);

POLYMERS;

ALKYNE DERIVATIVE; AMPHOPHILE; AZIDE; COPOLYMER; COPPER; COPPER SULFATE; HALIDE; IMIDAZOLE DERIVATIVE; LIGAND; ORGANIC COMPOUND; POLY(N ISOPROPYLACRYLAMIDE CO N VINYLIMIDAZOLE); POLYACRYLAMIDE; POLYMER; SODIUM AZIDE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CLICK CHEMISTRY; CYCLIZATION; CYCLOADDITION; DIPOLE; PARTICLE SIZE; SCANNING ELECTRON MICROSCOPY; SOLID; SOLUBILITY; SURFACE PROPERTY; X RAY PHOTOELECTRON SPECTROSCOPY;

ACRYLAMIDES; CATALYSIS; CLICK CHEMISTRY; COPPER; IMIDAZOLES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; SURFACE-ACTIVE AGENTS;

EID: 84861850402     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3036543     Document Type: Article

References (68)

1. Karlin, K. D.; Cruse, R. W.; Gultneh, Y.; Farooq, A.; Hayes, J. C.; Zubieta, J. J. Am. Chem. Soc. 1987, 109, 2668
2. Sadava, D.; Hillis, D. M.; Heller, H. C.; Berenbaum, M. R. Life: The Science of Biology: Evolution, Diversity, and Ecology; W H Freeman & Co.: New York, 2009.
3. Coelho, A.; Diz, P.; Caamaño, O.; Sotelo, E. Adv. Synth. Catal. 2010, 352, 1179
4. Girard, C.; Önen, E.; Aufort, M.; Beauviére, S.; Samson, E.; Herscovici, J. Org. Lett. 2006, 8, 1689
5. Park, I. S.; Kwon, M. S.; Kim, Y.; Lee, J. S.; Park, J. Org. Lett. 2008, 10, 497
6. Lipshutz, B. H.; Taft, B. R. Angew. Chem., Int. Ed. 2006, 45, 8235
7. Chassaing, S.; Sido, A. S. S.; Alix, A.; Kumarraja, M.; Pale, P.; Sommer, J. Chem.-Eur. J. 2008, 14, 6713
8. Chassaing, S.; Kumarraja, M.; Sido, A. S. S.; Pale, P.; Sommer, J. Org. Lett. 2007, 9, 883
9. Namitharan, K.; Kumarraja, M.; Pitchumani, K. Chem.-Eur. J. 2009, 15, 2755
10. Wang, Y.; Liu, J.; Xia, C. Adv. Synth. Catal. 2011, 353, 1534
11. Liu, M.; Reiser, O. Org. Lett. 2011, 13, 1102
12. Yamaguchi, K.; Oishi, T.; Katayama, T.; Mizuno, N. Chem.-Eur. J. 2009, 15, 10464
13. Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Adv. Synth. Catal. 2010, 352, 3208
14. Jin, T.; Yan, M.; Menggenbateer; Minato, T.; Bao, M.; Yamamoto, Y. Adv. Synth. Catal. 2011, 353, 3095
15. Megia-Fernandez, A.; Ortega-Muñoz, M.; Lopez-Jaramillo, J.; Hernandez-Mateo, F.; Santoyo-Gonzaleza, F. Adv. Synth. Catal. 2010, 352, 3306
16. Chen, W.; Boven, G.; Challa, G. Macromolecules 1991, 24, 3982
17. Zeitler, K.; Mager, I. Adv. Synth. Catal. 2007, 349, 1851
18. Arai, T.; Mizukami, T.; Yanagisawa, A. Org. Lett. 2007, 9, 1145
19. Arai, T.; Yokoyama, N.; Yanagisawa, A. Chem.-Eur. J. 2008, 14, 2052
20. Sarkar, S. M.; Uozumi, Y.; Yamada, Y. M. A. Angew. Chem., Int. Ed. 2011, 50, 9437
21. Yamada, Y. M. A.; Sarkar, S. M.; Uozumi, Y. J. Am. Chem. Soc. 2012, 134, 3190
22. Yamada, Y. M. A. Chem. Pharm. Bull. 2005, 53, 723
23. Yamada, Y. M. A.; Uozumi, Y. Org. Lett. 2006, 8, 1375
24. Uozumi, Y.; Yamada, Y. M. A.; Beppu, T.; Fukuyama, N.; Ueno, M.; Kitamori, T. J. Am. Chem. Soc. 2006, 128, 15994
25. Yamada, Y. M. A.; Maeda, Y.; Uozumi, Y. Org. Lett. 2006, 8, 4259
26. Yamada, Y. M. A.; Guo, H.; Uozumi, Y. Org. Lett. 2007, 9, 1501
27. Yamada, Y. M. A.; Uozumi, Y. Tetrahedron 2007, 63, 8492
28. Yamada, Y. M. A.; Jin, C.; Uozumi, Y. Org. Lett. 2010, 12, 4540
29. Yamada, Y. M. A.; Watanabe, T.; Torii, K.; Beppu, T.; Fukuyama, N.; Uozumi, U. Chem.-Eur. J. 2010, 16, 11311
30. Ohta, H.; Uozumi, Y.; Yamada, Y. M. A. Org. Lett. 2011, 13, 3892
31. Sarkar, B.; Wigfield, Y. J. Biol. Chem. 1967, 242, 5572
32. Peral, F.; Gallego, E. J. Mol. Struct. 1997, 415, 187
33. Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057
34. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596
35. Huisgen, R. Angew. Chem., Int. Ed. 1963, 2, 565
36. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004
37. Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51
38. Lutz, J.-F. Angew. Chem., Int. Ed. 2007, 46, 1018
39. Xiao, J. P.; Tolbert, T. J. Org. Lett. 2009, 11, 4144
40. Mohapatra, D. K.; Maity, P. K.; Shabab, M.; Khan, M. I. Bioorg. Med. Chem. Lett. 2009, 19, 5241
41. Pearson, D.; Downard, A. J.; Muscroft-Taylor, A.; Abel, A. D. J. Am. Chem. Soc. 2007, 129, 14862
42. Aragão-Leoneti, V.; Campo, V. L.; Gomes, A. S.; Field, R. A.; Carvalho, I. Tetrahedron 2010, 66, 9475
43. Iha, R. K.; Wooley, K. L.; Nystrcm, A. M.; Burke, D. J.; Kade, M. J.; Hawker, C. J. Chem. Rev. 2009, 109, 5620
44. Xia, Y.; Li, W.; Qu, F.; Fan, Z.; Liu, X.; Berro, C.; Rauzy, E.; Peng, L. Org. Biomol. Chem. 2007, 5, 1695
45. Brik, A.; Wu, C. Y.; Wong, C. H. Org. Biomol. Chem. 2006, 4, 1446
46. Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128
47. Lee, S. M.; Chen, H.; OHalloran, T. V.; Nguyen, S. T. J. Am. Chem. Soc. 2009, 131, 9311
48. Chernykh, A.; Agag, T.; Ishida, H. Polymer 2009, 50, 382
49. Li, B. L.; Liu, Z. T.; He, Y. M.; Pan, J.; Fan, Q. H. Polymer 2008, 49, 1527
50. Whittaker, M. R.; Urbani, C. N.; Monteiro, M. J. J. Am. Chem. Soc. 2006, 128, 11360
51. Lutz, J.-F. Angew. Chem., Int. Ed. 2007, 46, 1018
52. Sommer, S.; Weikart, N. D.; Brockmeyer, A.; Janning, P.; Mootz, H. D. Angew. Chem., Int. Ed. 2011, 50, 9888
53. Lallana, E.; Riguera, R.; Fernandez-Megia, E. Angew. Chem., Int. Ed. 2011, 50, 8794
54. Clavé, G.; Campidelli, S. Chem. Sci. 2011, 2, 1887
55. Binder, W. H.; Sachsenhofer, R. Macromol. Rapid Commun. 2007, 28, 15
56. Uozumi, Y.; Hayashi, T. Solid-Phase Palladium Catalysis for High-throughput Organic Synthesis. In Handbook of Combinatorial Chemistry; Nicolaou, K. C.; Hanko, R.; Hartwig, W., Eds.; Wiley-VCH: Weinheim, 2002.
57. Franzel, T.; Solodenko, W.; Kirschning, A. Solid-Phase Bound Catalysts: Properties and Applications. In Polymeric Materials in Organic Synthesis and Catalysis; Buchmeiser, M. R., Ed.; Wiley-VCH: Weinheim, 2003.
58. Uozumi, Y. Top. Curr. Chem. 2004, 242, 77
59. Wennemers, H. Combinatorial Methods for the Discovery of Catalysts. In Highlights in Bioorganic Chemistry; Schmuck, C.; Wennemers, H., Eds.; Wiley-VCH: Weinheim, 2004; p 436.
60. Wang, Z.; Chen, G.; Ding, K. Chem. Rev. 2009, 109, 322
61. Lu, J.; Toy, P. H. Chem. Rev. 2009, 109, 815
62. Baer, K.; Krausser, M.; Burda, E.; Hummel, W.; Berkessel, A.; Gröger, H. Angew. Chem., Int. Ed. 2009, 48, 9355
63. Uozumi, Y.; Yamada, Y. M. A. Chem. Rec. 2009, 9, 51
64. Lamblin, M.; Nassar-Hardy, L.; Hierso, J.-C.; Fouquet, E.; Felpin, F.-X. Adv. Synth. Catal. 2010, 352, 33
65. Yamada, Y. M. A.; Uozumi, Y. J. Synth. Org. Chem. Jpn. 2011, 69, 542
66. For a review, see: Phan, N. T. S.; Van Der Sluys, M.; Jones, C. W. Adv. Synth. Catal. 2006, 348, 609
67. Shao, C.; Cheng, G.; Su, D.; Xu, J.; Wang, X.; Hu, Y. Adv. Synth. Catal. 2010, 352, 1587-1592
68. Khairul, W. M.; Fox, M. A.; Zaitseva, N. N.; Gaudio, M.; Yufit, D. S.; Skelton, B. W.; White, A. H.; Howard, J. A. K.; Bruce, M. I.; Low, P. J. Dalton Trans. 2009, 610-620