Synthesis and characterization of organolanthanide complexes with a calix[4]-pyrrolyl ligand and their catalytic activities toward hydrophosphonylation of aldehydes and unactivated ketones

Organometallics

Volumn 31, Issue 5, 2012, Pages 1696-1702

  Zhou, Shuangliu ^a   Wang, Hengyu ^a   Ping, Jian ^a   Wang, Shaowu ^a,b   Zhang, Lijun ^a   Zhu, Xiancui ^a   Wei, Yun ^a   Wang, Fenhua ^a   Feng, Zhijun ^a   Gu, Xiaoxia ^a   Yang, Song ^a   Miao, Hui ^a  

^a ANHUI NORMAL UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALI METAL SALTS; AMIDO COMPLEXES; CATALYST LOADINGS; DINUCLEAR; EFFICIENT CATALYSTS; ELIMINATION REACTION; HIGH YIELD; HYDROPHOSPHONYLATION; LANTHANIDE AMIDES; ORGANOLANTHANIDE COMPLEXES; PYRROLYL; PYRROLYL LIGANDS; ROOM TEMPERATURE; SILYLAMINE; SINGLE CRYSTAL X-RAY ANALYSIS;

ALDEHYDES; AMIDES; CATALYST ACTIVITY; CHELATION; CHLORINE COMPOUNDS; GADOLINIUM; KETONES; NEODYMIUM; SYNTHESIS (CHEMICAL); TOLUENE; X RAY ANALYSIS;

ORGANIC COMPOUNDS;

EID: 84863292918     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om2008925     Document Type: Article

References (68)

1. Hart, F. A. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., and McCleverty, J. A., Eds.; Pergamon: Oxford, U.K., 1987; Vol. 3, Chapter 39.
2. Campazzi, E.; Solari, E.; Scopelliti, R.; Floriani, C. Inorg. Chem. 1999, 38, 6240-6245
3. Dubé, T.; Guan, J.; Gambarotta, S.; Yap, G. P. A. Chem.-Eur. J. 2001, 7, 374-381
4. Jubb, J.; Gambarotta, S. J. Am. Chem. Soc. 1994, 116, 4477-4478
5. Campazzi, E.; Solari, E.; Floriani, C.; Scopelliti, R. Chem. Commun. 1998, 2603-2604
6. Dubé, T.; Gambarotta, S.; Yap, G. P. A. Angew. Chem., Int. Ed. 1999, 38, 1432-1435
7. Guan, J.; Dubé, T.; Gambarotta, S.; Yap, G. P. A. Organometallics 2000, 19, 4820-4827
8. Dubé, T.; Gambarotta, S.; Yap, G. P. A. Organometallics 2000, 19, 121-126
9. Dubé, T.; Gambarotta, S.; Yap, G. P. A. Organometallics 2000, 19, 817-823
10. Wang, J.; Dick, A. K. J.; Gardiner, M. G.; Yates, B. F.; Peacock, E. J.; Skelton, B. W.; White, A. H. Eur. J. Inorg. Chem. 2004, 1992-1995
11. Wang, J.; Gardiner, M. G.; Skelton, B. W.; White, A. H. Organometallics 2005, 24, 815-818
12. Wang, J.; Amos, R. I. J.; Frey, A. S. P.; Gardiner, M. G.; Cole, M. L.; Junk, P. C. Organometallics 2005, 24, 2259-2261
13. Frey, A. S. P.; Gardiner, M. G.; Stringer, D. N.; Yates, B. F.; George, A. V.; Jensen, P.; Turner, P. Organometallics 2007, 26, 1299-1302
14. Zhou, S.; Wu, S.; Zhu, H.; Wang, S.; Zhu, X.; Zhang, L.; Yang, G.; Cui, D.; Wang, H. Dalton Trans. 2011, 40, 9447-9453
15. Hilderbrand, R. L., Ed. The Role of Phosphonates in Living Systems; RC Press: Boca Raton, FL, 1983.
16. Engel, R. Handbook of Organophosphorus Chemistry; Marcel Dekker: New York, 1992.
17. Szymańska, A.; Szymczak, M.; Boryski, J.; Stawinski, J.; Kraszewski, A.; Collu, G.; Sanna, G.; Giliberti, G.; Loddo, R.; Colla, P. L. Bioorg. Med. Chem. 2006, 14, 1924
18. Demmer, C. S.; Krogsgaard-Larsen, N.; Bunch, L. Chem. Rev. 2011, 111, 7981-8006
19. Pudovik, A. N.; Konovalova, I. V. Synthesis 1979, 81
20. Gröger, H.; Hammer, B. Chem.-Eur. J. 2000, 6, 943-948
21. Merino, P.; Marqués-López, E.; Herrera, R. P. Adv. Synth. Catal. 2008, 350, 1195-1208
22. Duxbury, J. P.; Cawley, A.; Thornton-Pett, M.; Wantz, L.; Warne, J. N. D.; Greatrex, R.; Brown, D.; Kee, T. P. Tetrahedron Lett. 1999, 40, 4403-4406
23. Duxbury, J. P.; Warne, J. N. D.; Mushtaq, R.; Ward, C.; Thornton-Pett, M.; Jiang, M.; Greatrex, R.; Kee, T. P. Organometallics 2000, 19, 4445-4457
24. Saito, B.; Katsuki, T. Angew. Chem., Int. Ed. 2005, 44, 4600-4602
25. Saito, B.; Egami, H.; Katsuki, T. J. Am. Chem. Soc. 2007, 129, 1978-1986
26. Zhou, X.; Liu, X.; Yang, X.; Shang, D.; Xin, J.; Feng, X. Angew. Chem., Int. Ed. 2008, 47, 392-394
27. Gou, S.; Zhou, X.; Wang, J.; Liu, X.; Feng, X. Tetrahedron 2008, 64, 2864-2870
28. Corey, E. J.; Lee, T. W. Chem. Commun. 2001, 1321-1329
29. Suyama, K.; Sakai, Y.; Matsumoto, K.; Saito, B.; Katsuki, T. Angew. Chem., Int. Ed. 2010, 49, 797-799
30. Yokomatsu, T.; Yamgishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1993, 4, 1779-1782
31. Groaning, M. D.; Rowe, B. J.; Spilling, C. D. Tetrahedron Lett. 1998, 39, 5485-5488
32. Yang, F.; Zhao, D.; Lan, J.; Xi, P.; Yang, L.; Xiang, S.; You, J. Angew. Chem., Int. Ed. 2008, 47, 5646-5649
33. Jung, M. E.; Cordova, J.; Murakami, M. Org. Lett. 2009, 11, 3882
34. Yokomatsu, T.; Yamgishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1993, 4, 1783-1784
35. Yokomatsu, T.; Yamgishi, T.; Shibuya, S. J. Chem. Soc., Perkin Trans. 1 1997, 1527-1533
36. Sasai, H.; Bougauchi, M.; Arai, T.; Shibasaki, M. Tetrahedron Lett. 1997, 38, 2717-2720
37. Rath, N. P.; Spilling, C. D. Tetrahedron Lett. 1994, 35, 227-230
38. Arai, T.; Bougauchi, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1996, 61, 2926-2927
39. Qian, C.; Huang, T.; Zhu, C.; Sun, J. J. Chem. Soc., Perkin Trans. 1 1998, 2097-2103
40. Di Bari, L.; Lelli, M.; Salvadori, P. Chem.-Eur. J. 2004, 10, 4594-4598
41. Wu, Q.; Zhou, J.; Yao, Z.; Xu, F.; Shen, Q. J. Org. Chem. 2010, 75, 7498-7501
42. Chen, W.; Hui, Y.; Zhou, X.; Jiang, J.; Cai, Y.; Liu, X.; Lin, L.; Feng, X. Tetrahedron Lett. 2010, 51, 4175-4178
43. Thottempudi, V.; Chung, K.-H. Bull. Korean Chem. Soc. 2008, 29, 1781-1783
44. de Noronha, R. G.; Costa, P. J.; Romao, C. C.; Calhorda, M. J.; Fernandes, A. C. Organometallics 2009, 28, 6206-6212
45. Wang, F.; Liu, X.; Cui, X.; Xiong, Y.; Zhou, X.; Feng, X. Chem.-Eur. J. 2009, 15, 589
46. Texier-Boullet, F.; Foucaud, A. Synthesis 1982, 165
47. Texier-Boullet, F.; Lequitte, M. Tetrahedron Lett. 1986, 27, 3515
48. Sebti, S.; Rhihil, A.; Saber, A.; Laghrissi, M.; Boulaajaj, S. Tetrahedron Lett. 1996, 37, 3999
49. Samanta, S.; Zhao, C.-G. J. Am. Chem. Soc. 2006, 128, 7442
50. Mandal, T.; Samanta, S.; Zhao, C.-G. Org. Lett. 2007, 9, 943
51. Liu, J.; Yang, Z.; Wang, Z.; Wang, F.; Chen, X.; Liu, X.; Feng, X.; Su, Z.; Hu, C. J. Am. Chem. Soc. 2008, 130, 5654-5655
52. Chen, X.; Wang, J.; Zhu, Y.; Shang, D.; Gao, B.; Liu, X.; Feng, X.; Su, Z.; Hu, C. Chem.-Eur. J. 2008, 14, 10896
53. Ruveda, M. A.; De Licastro, S. A. Tetrahedron 1972, 28, 6012
54. Kharasch, M. S.; Mosher, R. A.; Bengelsdorf, I. S. J. Org. Chem. 1960, 25, 1000
55. Simoni, D.; Invidiata, F. P.; Manferdini, M.; Lampronti, I.; Rondanin, R.; Roberti, M.; Pollini, G. P. Tetrahedron Lett. 1998, 39, 7615
56. Maeda, H.; Takahashi, K.; Ohmori, H. Tetrahedron 1998, 54, 12233
57. Demir, A. S.; Reis, O.; Igdir, A. C.; Esiringue, I.; Eymur, S. J. Org. Chem. 2005, 70, 10584
58. El Kam, L.; Gaultier, L.; Grimaud, L.; Dos Santos, A. Synlett 2005, 2335
59. Demir, A. S.; Esiringu, I.; Gollu, M.; Reis, O. J. Org. Chem. 2009, 74, 2197
60. Zhou, X.; Liu, Y.; Chang, L.; Zhao, J.; Shang, D.; Liu, X.; Lin, L.; Feng, X. Adv. Synth. Catal. 2009, 351, 2567-2572
61. Zhou, X.; Zhang, Q.; Hui, Y.; Chen, W.; Jiang, J.; Lin, L.; Liu, X.; Feng, X. Org. Lett. 2010, 12, 4296-4299
62. Liu, C.; Zhou, S.; Wang, S.; Zhang, L.; Yang, G. Dalton Trans. 2010, 39, 8994-8999
63. Zhou, S.; Wang, S.; Yang, G.; Li, Q.; Zhang, L.; Yao, Z.; Zhou, Z.; Song, H. Organometallics 2007, 26, 3755-3761
64. Zhou, S.; Wang, S.; Yang, G.; Liu, X.; Sheng, E.; Zhang, K.; Cheng, L.; Huang, Z. Polyhedron 2003, 22, 1019-1024
65. Sheng, E.; Wang, S.; Yang, G.; Zhou, S.; Cheng, L.; Zhang, K.; Huang, Z. Organometallics 2003, 22, 684-692
66. Gale, P. A.; Sessler, J. L.; Král, V.; Lynch, V. J. Am. Chem. Soc. 1996, 118, 5140-5141
67. Sheldrick, G. M. SADABS: Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen: Göttingen, Germany, 1996.
68. Sheldrick, G. M. HELXTL 5.10 for Windows NT: Structure Determination Software Programs; Bruker Analytical X-ray Systems, Inc.: Madison, WI, 1997.