Recyclable porous polymer-supported copper catalysts for Glaser and Huisgen 1,3-diolar cycloaddition reactions

Chemistry - An Asian Journal

Volumn 8, Issue 11, 2013, Pages 2822-2827

  Sun, Qi ^a   Lv, Zhonfei ^a   Du, Yuyang ^a   Wu, Qinming ^a   Wang, Liang ^a,b   Zhu, Longfeng ^b   Meng, Xiangju ^a   Chen, Wanzhi ^a   Xiao, Feng Shou ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b JILIN UNIVERSITY   (China)

Author keywords

copper; Glaser coupling; heterogeneous catalysis; Huisgen 1,3 dipolar cycloaddition; phenanthroline ligand; polymers

Indexed keywords

1 ,3-DIPOLARCYCLOADDITION; CATALYST LOADINGS; COORDINATION ABILITY; CYCLOADDITION REACTION; GLASER COUPLINGS; HIERARCHICAL POROSITY; LARGE PORE VOLUME; PHENANTHROLINES;

ACRYLIC MONOMERS; AMIDES; CATALYSIS; COPOLYMERIZATION; COPOLYMERS; COPPER; CYCLOADDITION; HYDROCARBONS; LOADING; POLYMERS; POLYSTYRENES; SCANNING ELECTRON MICROSCOPY; THERMOGRAVIMETRIC ANALYSIS; TRANSMISSION ELECTRON MICROSCOPY;

CATALYSTS;

COPPER; PHENANTHROLINE DERIVATIVE; POLYMER;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLOADDITION; GLASER COUPLING; HETEROGENEOUS CATALYSIS; HUISGEN 1,3-DIPOLAR CYCLOADDITION; PHENANTHROLINE LIGAND; POROSITY;

COPPER; GLASER COUPLING; HETEROGENEOUS CATALYSIS; HUISGEN 1,3-DIPOLAR CYCLOADDITION; PHENANTHROLINE LIGAND; POLYMERS;

CATALYSIS; COPPER; CYCLOADDITION REACTION; PHENANTHROLINES; POLYMERS; POROSITY;

EID: 84887022141     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201300690     Document Type: Article

References (75)

1. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457
2. L. Yin, J. Liebscher, Chem. Rev. 2007, 107, 133
3. C. Wei, C.-J. Li, J. Am. Chem. Soc. 2003, 125, 9584
4. J. Magano, J. R. Dunetz, Chem. Rev. 2011, 111, 2177
5. N. E. Leadbeater, M. Marco, Chem. Rev. 2002, 102, 3217
6. W. Watanabe, T. Maekawa, Y. Miyazaki, T. Kida, K. Takeshita, A. Mori, Chem. Asian J. 2012, 7, 1679
7. S. G. Agalave, S. R. Maujan, V. S. Pore, Chem. Asian J. 2011, 6, 2696.
8. R. Marion, G. Muthusamy, F. Geneste, J. Catal. 2012, 286, 266
9. J. R. Cabrero-Antonino, T. García, P. Rubio-Marqués, J. A. Vidal-Moya, A. Leyva-Pérez, S. S. Al-Deyab, S. I. Al-Resayyes, U. Díaz, A. Corma, ACS Catal. 2011, 1, 147
10. S. Kamijo, Y. Yamamoto, Angew. Chem. 2002, 114, 3364
11. Angew. Chem. Int. Ed. 2002, 41, 3230
12. M. E. Sad, M. Neurock, E. Iglesia, J. Am. Chem. Soc. 2011, 133, 20384
13. J. M. Hoover, S. S. Stahl, J. Am. Chem. Soc. 2011, 133, 16901
14. G. O. Jones, P. Liu, K. N. Houk, S. L. Buchwald, J. Am. Chem. Soc. 2010, 132, 6205
15. P. Gamez, I. W. C. E. Arends, R. A. Sheldon, J. Reedijk, Adv. Synth. Catal. 2004, 346, 805
16. Y. Liu, W. Yan, Y. Chen, J. L. Petersen, X. Shi, Org. Lett. 2008, 10, 5389.
17. F. Monnier, M. Taillefer, Angew. Chem. 2009, 121, 7088
18. Angew. Chem. Int. Ed. 2009, 48, 6954
19. S. Benyahya, F. Monnier, M. Tailefer, M. W. C. Man, C. Bied, F. Ouazzani, Adv. Synth. Catal. 2008, 350, 2205
20. E. Zuidema, C. Bolm, Chem. Eur. J. 2010, 16, 4181
21. Y. Zhang, S. Patel, N. Mainolfi, Chem. Sci. 2012, 3, 3196.
22. J. J. Spivey, A. Egbebi, Chem. Soc. Rev. 2007, 36, 1514
23. L. Canali, D. C. Sherrington, Chem. Soc. Rev. 1999, 28, 85
24. Q.-H. Fan, Y.-M. Li, A. S. C. Chan, Chem. Rev. 2002, 102, 3385
25. S. Minakata, M. Komatsu, Chem. Rev. 2009, 109, 711
26. C. A. McNamara, M. J. Dixon, M. Bradley, Chem. Rev. 2002, 102, 3275
27. D. E. De Vos, M. Dams, B. F. Sels, P. A. Jacobs, Chem. Rev. 2002, 102, 3615.
28. Q. Sun, X. Meng, X. Liu, X. Zhang, Y. Yang, Q. Yang, F.-S. Xiao, Chem. Commun. 2012, 48, 10505
29. F. Liu, L. Wang, Q. Sun, L. Zhu, X. Meng, F.-S. Xiao, J. Am. Chem. Soc. 2012, 134, 16948
30. F. Liu, W. Li, Q. Sun, L. Zhu, X. Meng, Y.-H. Guo, F.-S. Xiao, ChemSusChem 2011, 4, 1059
31. F. Liu, W. Kong, C. Qi, L. Zhu, F.-S. Xiao, ACS Catal. 2012, 2, 565.
32. J. D. Crowley, S. M. Goldup, N. D. Gowans, D. A. Leigh, J. Am. Chem. Soc. 2010, 132, 6243
33. T. Hamada, X. Ye, S. S. Stahl, J. Am. Chem. Soc. 2008, 130, 833
34. Y. Gao, G. Wang, L. Chen, P. Xu, Y. Zhao, Y. Zhou, L.-B. Han, J. Am. Chem. Soc. 2009, 131, 7956.
35. W. Mo, H. Liu, H. Xiong, M. Li, G. Li, Appl. Catal. A 2007, 333, 172
36. Q. Kang, J. Luo, Y. Bai, Z. Yang, Z. Lei, J. Organomet. Chem. 2005, 690, 6309.
37. P. Siemsen, R. C. Livingston, F. Diederich, Angew. Chem. 2000, 112, 2740
38. Angew. Chem. Int. Ed. 2000, 39, 2632
39. J. B. Ravnsbæk, M. F. Jacobsen, C. B. Rosen, N. V. Voigt, K. V. Gothelf, Angew. Chem. 2011, 123, 11043
40. Angew. Chem. Int. Ed. 2011, 50, 10851
41. D. Astruc, L. Liang, A. Papakousiou, J. Ruiz, Acc. Chem. Res. 2012, 45, 630
42. M. Auer, M. Schneider, A. Baiker, J. Chem. Soc. Chem. Commun. 1995, 2057
43. Y. Wang, J. Liu, C. Xia, Adv. Synth. Catal. 2011, 353, 1534
44. Y. He, C. Cai, Catal. Sci. Technol. 2012, 2, 1126
45. R. Xiao, R. Yao, M. Cai, Eur. J. Org. Chem. 2012, 4178
46. A. Leyva-Pérez, A. Doménech, S. I. Al-Resayes, A. Corma, ACS Catal. 2012, 2, 121.
47. P. Kuhn, A. Alix, M. Kumarraja, B. Louis, P. Pale, J. Sommer, Eur. J. Org. Chem. 2009, 423
48. K. Kamata, S. Yamaguchi, M. Kotani, K. Yamaguchi, N. Mizuno, Angew. Chem. 2008, 120, 2441
49. Angew. Chem. Int. Ed. 2008, 47, 2407
50. T. Oishi, T. Katayama, K. Yamaguchi, N. Mizuno, Chem. Eur. J. 2009, 15, 7539
51. T. Oishi, K. Yamaguchi, N. Mizuno, ACS Catal. 2011, 1, 1351
52. F. Alonso, T. Melkonian, Y. Moglie, M. Yus, Eur. J. Org. Chem. 2011, 2524
53. F. Alonso, Y. Miguel, ACS Catal. 2012, 2, 1441.
54. R. Kam, C. Selomulya, R. Amal, J. Scott, J. Catal. 2010, 273, 73
55. W.-L. Dai, Q. Sun, J.-F. Deng, D. Wu, Y.-H. Sun, Appl. Surf. Sci. 2001, 177, 172.
56. W. S. Brotherton, H. A. Michaels, J. T. Simmons, R. J. Clark, N. S. Dalal, L. Zhu, Org. Lett. 2009, 11, 4954.
57. R. Schmidt, R. Thorwirth, T. Szuppa, A. Stolle, B. Ondruschka, H. Hopf, Chem. Eur. J. 2011, 17, 8129
58. B. H. Lipshutz, B. R. Taft, Angew. Chem. 2006, 118, 8415
59. Angew. Chem. Int. Ed. 2006, 45, 8235
60. A. Coelho, P. Diz, O. Caamaño, E. Sotelo, Adv. Synth. Catal. 2010, 352, 1179
61. M. Chtchigrovsky, A. Primo, P. Gonzalez, K. Molvinger, M. Robitzer, F. Quignard, F. Taran, Angew. Chem. 2009, 121, 6030-6034
62. Angew. Chem. Int. Ed. 2009, 48, 5916-5920
63. R. B. N. Baig, R. S. Varma, Green Chem. 2012, 14, 625
64. Y. Monguchi, K. Nozaki, T. Maejima, Y. Shimoda, Y. Sawama, Y. Kitamura, Y. Kitade, H. Sajiki, Green Chem. 2013, 15, 490
65. C. Cirard, E. Önen, M. Aufort, S. Beauvière, E. Samson, J. Herscovici, Org. Lett. 2006, 8, 1689
66. H. Koga, A. Azetsu, E. Tokunaga, T. Saito, A. Isogai, T. Kitaoka, J. Mater. Chem. 2012, 22, 5538
67. Y. M. A. Yamada, S. M. Sarkar, Y. Uozumi, J. Am. Chem. Soc. 2012, 134, 9285
68. I. R. Baxendale, S. V. Ley, A. C. Mansfield, C. D. Smith, Angew. Chem. 2009, 121, 4077
69. Angew. Chem. Int. Ed. 2009, 48, 4017
70. B. Dervaux, F. E. Du Prez, Chem. Sci. 2012, 3, 959
71. S. B. Ötvös, I. M. Mándity, L. Kiss, F. Fülöp, Chem. Asian J. 2013, 8, 800
72. W. Wang, S. Hong, A. Tran, H. Jiang, R. Triano, Y. Liu, X. Chen, P. Wu, Chem. Asian J. 2011, 6, 2796.
73. P. Wu, A. K. Feldman, A. K. Nugent, C. J. Hawker, A. Scheel, B. Voit, J. Pyun, J. M. J. Fréchet, K. B. Sharpless, V. V. Fokin, Angew. Chem. 2004, 116, 4018
74. Angew. Chem. Int. Ed. 2004, 43, 3928.
75. V. O. Rodionov, S. I. Presolski, D. D. Diaz, V. V. Fokin, M. G. Finn, J. Am. Chem. Soc. 2007, 129, 12705.