An efficient and recyclable silica-supported carbene-Cu(II) catalyst for the oxidative coupling reaction of terminal alkynes with H-phosphonates under base-free reaction conditions

Applied Organometallic Chemistry

Volumn 25, Issue 11, 2011, Pages 830-835

  Liu, Ping ^a   Yang, Jin ^a   Li, Pinhua ^a   Wang, Lei ^a,b  

^a HUAIBEI NORMAL UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

H phosphonates; NHC Cu(II); Recyclibility; Silica supported catalyst; Terminal alkynes

Indexed keywords

H-PHOSPHONATES; NHC-CU(II); RECYCLIBILITY; SILICA-SUPPORTED CATALYSTS; TERMINAL ALKYNES;

CATALYST SUPPORTS; CHEMICAL REACTIONS; SILICA; SILICON COMPOUNDS;

ACETYLENE;

EID: 84155162800     PISSN: 02682605     EISSN: 10990739     Source Type: Journal    
DOI: 10.1002/aoc.1847     Document Type: Article

References (61)

1. a) A. Schwan, Chem. Soc. Rev. 2004, 33, 218;
2. L.-B. Han, M. Tanaka, J. Am. Chem. Soc. 1996, 118, 1571;
3. L.-B. Han, M. Tanaka, Chem. Commun. 1999, 395;
4. L.-B. Han, Y. Ono, S. Shimada, J. Am. Chem. Soc. 2008, 130, 2752;
5. (e) M. Niu, H. Fu, Y. Jiang, Y. Zhao, Chem. Commun. 2007, 272;
6. L. Coudray, J. Montchamp, Eur. J. Org. Chem. 2008, 3601;
7. D. Prim, J. Campagne, D. Joseph, B. Andrioletti, Tetrahedron 2002, 58, 2041.
8. a) B. Iorga, F. Eymery, D. Carmichael, P. Savignac, Eur. J. Org. Chem. 2000, 3103;
9. M. Lera, C. J. Hayes, Org. Lett. 2000, 2, 3873.
10. Y. Gao, G. Wang, L. Chen, P. Xu, Y. Zhao, Y. Zhou, L.-B. Han, J. Am. Chem. Soc. 2009, 131, 7956.
11. a) W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Chem. Eur. J. 1996, 2, 772;
12. W. A. Herrmann, C. Köcher, Angew. Chem. Int. Ed. 1997, 36, 2162;
13. M. G. Gardiner, W. A. Herrmann, C. P. Reisinger, J. Schwarz, M. Spiegler, J. Organomet. Chem. 1999, 572, 239;
14. N. Marion, S. P. Nolan, Acc. Chem. Res. 2008, 41, 1440;
15. S. Würtz, F. Glorius, Acc. Chem. Res. 2008, 41, 1523;
16. X. Zhang, Q. Xia, W. Chen, Dalton Trans. 2009, 7045.
17. A. J. Arduengo, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1991, 113, 361.
18. a) C. Yang, S. P. Nolan, Organometallics 2002, 21, 1020;
19. G. A. Grasa, S. P. Nolan, Org. Lett. 2001, 3, 119;
20. S. B. Blakey, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 6046;
21. J. Liu, M. Robins, Org. Lett. 2004, 6, 3421;
22. J. Liu, M. Robins, Org. Lett. 2005, 7, 1149.
23. a) L. R. Titcomb, S. Caddick, F. G. N. Cloke, D. J. Wilson, D. McKerrecher, Chem. Commun. 2001, 1388;
24. M. S. Viciu, R. M. Kissling, E. D. Stevens, S. P. Nolan, Org. Lett. 2002, 4, 2229;
25. M. S. Viciu, R. A. Kelly, E. D. Stevens, F. Naud, M. Studer, S. P. Nolan, Org. Lett. 2003, 5, 1479.
26. a) S. J. Connon, S. Blechert, Angew. Chem. Int. Ed. 2003, 42, 1900;
27. T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18;
28. R. E. Giudici, A. H. Hoveyda, J. Am. Chem. Soc. 2007, 129, 3824;
29. T. Ritter, M. W. Day, R. H. Grubbs, J. Am. Chem. Soc. 2006, 128, 11768;
30. S. H. Hong, A. G. Wenzel, T. T. Salguero, M. W. Day, R. H. Grubbs, J. Am. Chem. Soc. 2007, 129, 7961.
31. a) E. F. Connor, G. W. Nyce, M. Myers, A. Mock, J. L. Hedrick, J. Am. Chem. Soc. 2002, 124, 914;
32. W. Li, H. Sun, M. Chen, Z. Wang, D. Hu, Q. Shen, Y. Zhang, Organometallics 2005, 24, 5925;
33. E. Jellema, P. H. M. Budzelaar, J. N. H. Reek, B. de Bruin, J. Am. Chem. Soc. 2007, 129, 11631;
34. S. T. Diver, A. A. Kulkarni, D. A. Clark, B. P. Peppers, J. Am. Chem. Soc. 2007, 129, 5832.
35. A. J. Arduengo, H. V. R. Dias, J. C. Calabrese, F. Davidson, Organometallics 1993, 12, 3405.
36. P. K. Fraser, S. Woodward, Tetrahedron Lett. 2001, 42, 2747.
37. J. Yun, D. Kim, H. Yun, Chem. Commun. 2005, 5181.
38. a) S. P. Nolan, N-Heterocyclic Carbenes in Synthesis, Wiley-VCH: Weinheim, 2006;
39. F. Glorius, N-Heterocyclic Carbenes in Transition Metal Catalysis: Topics in Organometallic Chemistry, Springer: Berlin, 2006.
40. a) S. Díez-González, A. Correa, L. Cavallo, S. P. Nolan, Chem. Eur. J. 2006, 12, 7558;
41. Y. Wei, H. Zhao, J. Kan, W. Su, M. Hong, J. Am. Chem. Soc. 2010, 132, 2522;
42. T. Hamada, X. Ye, S. S. Stahl, J. Am. Chem. Soc. 2008, 130, 833;
43. M. Kitahara, K. Hirano, H. Tsurugi, T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 1772.
44. a) R. A. Sheldon, I. Arends, U. Hanefeld, Green Chemistry and Catalysis, Wiley-VCH: Weinheim, 2007;
45. C. E. Song, S. G. Lee, Chem. Rev. 2002, 102, 3495;
46. Z. L. Lu, E. Lindner, H. A. Mayer, Chem. Rev. 2002, 102, 3543;
47. C.-J. Liu, S.-G. Li, W.-Q. Pang, C.-M. Che, Chem. Commun. 1997, 65;
48. M. Lamblin, L. Nassar-Hardy, J. C. Hierso, E. Fouquet, F. X. Felpin, Adv. Synth. Catal. 2010, 352, 33;
49. Y. Kitamura, S. Sako, A. Tsutsui, Y. Monguchi, T. Maegaw, Y. Kitade, H. Sajikia, Adv. Synth. Catal. 2010, 352, 718;
50. P. Liu, C.-Y. Zhou, S. Xiang, C.-M. Che, Chem. Commun. 2010, 46, 2739.
51. a) M. Wang, P. Li, L. Wang, Eur. J. Org. Chem. 2008, 2255;
52. P. Li, L. Wang, Y. Zhang, Tetrahedron 2008, 64, 10825;
53. P. Li, L. Wang, Y. Zhang, M. Wang, Tetrahedron Lett. 2008, 49, 6650.
54. C. Neil, K. Elham, T. William, J. Org. Chem. 2009, 74, 5762.
55. R. Dizière, P. Savignac, Tetrahedron Lett. 1996, 37, 1783.
56. J. E. Hong, C.-W. Lee, Y. Kwon, D. Y. Oh, Synth. Commun. 1996, 26, 1563.
57. S. G. Dutremez, C. Guerin, B. J. L. Henner, V. Tomberli, Phosphorus, Sulfur Silicon Relat. Elem. 2000, 160, 251.
58. I. Pergament, M. Srebnik, Org. Lett. 2001, 3, 217.
59. M. G. Jun, W. S. Jin, P. P. Chan, D. Y. Oh, Synth. Commun. 1997, 27, 3171.
60. G. H. Roger, T. Stuart, Tetrahedron Lett. 1982, 25, 2603.
61. A. Kar, I. A. Sayyed, W. F. Lo, H. M. Kaiser, M. Beller, M. K. Tse, Org. Lett. 2007, 9, 3405.