Synthesis and structural characterization of palladacycles with polydentate ligands by a stepwise coupling route - Palladacycles containing halides as efficient catalysts and substrates

European Journal of Inorganic Chemistry

Volumn , Issue 31, 2011, Pages 4878-4888

  Xu, Chen ^a   Wang, Zhi Qiang ^a   Zhang, Ya Peng ^b   Dong, Xin Ming ^b   Hao, Xin Qi ^b   Fu, Wei Jun ^a   Ji, Bao Ming ^a   Song, Mao Ping ^b  

^a LUOYANG NORMAL UNIVERSITY   (China)

^b ZHENGZHOU UNIVERSITY   (China)

Author keywords

Amination; Halides; Homogeneous catalysis; Palladacycles; Palladium; Sandwich complexes

Indexed keywords

AMINATION; AMINES; CATALYSIS; CATALYSTS; CHELATION; LIGANDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SINGLE CRYSTALS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

COUPLING REACTION; CRYSTALS STRUCTURES; EFFICIENT CATALYSTS; FERROCENYL; HALIDE; HOMOGENEOUS CATALYSIS; PALLADACYCLES; POLYDENTATE LIGAND; SANDWICH COMPLEXES; SUZUKI-COUPLING REACTION;

PALLADIUM COMPOUNDS;

EID: 80054934974     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.201100617     Document Type: Article

References (87)

1. nd ed., Wiley-VCH, Weinheim, Germany, 2004.
2. nd ed., Wiley, Chichester, U. K., 2004.
3. For reviews, see
4. J. Dupont, M. Pfeffer, J. Spencer, Eur. J. Inorg. Chem. 2001, 1917.
5. R. B. Bedford, Chem. Commun. 2003, 1787.
6. J. Dupont, C. S. Consorti, J. Spencer, Chem. Rev. 2005, 105, 2527.
7. J. Vicente, I. Saura-Llamas, Comments Inorg. Chem. 2007, 28, 39.
8. J. Dupont, M. Pfeffer, Palladacycles, Wiley-VCH, Weinheim, Germany, 2008.
9. W. A. Herrmann, C. Brossmer, K. ãfele, C. P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989
10. Angew. Chem. Int. Ed. Engl. 1995, 34, 1844.
11. M. Beller, H. Fischer, W. A. Herrmann, K. ãfele, C. Brossmer, Angew. Chem. 1995, 107, 1992
12. Angew. Chem. Int. Ed. Engl. 1995, 34, 1848.
13. R. B. Bedford, S. L. Hazelwood, P. N. Horton, M. B. Hursthouse, Dalton Trans. 2003, 4164.
14. M. R. Biscoe, B. P. Fors, S. L. Buchwald, J. Am. Chem. Soc. 2008, 130, 6686.
15. C. Xu, J. F. Gong, S. F. Yue, Y. Zhu, Y. J. Wu, Dalton Trans. 2006, 4730.
16. C. Xu, J. F. Gong, Y. J. Wu, Tetrahedron Lett. 2007, 48, 1619.
17. C. Xu, Z. Q. Wang, W. J. Fu, X. H. Lou, Y. F. Li, F. F. Cen, H. J. Ma, B. M. Ji, Organometallics 2009, 28, 1909.
18. A. Togni, T. Hayashi, Ferrocenes, Homogeneous Catalysis, Organic Synthesis and Materials Sciences, VCH, Weinheim, Germany, 1995.
19. G. Zhao, Q. C. Yang, T. C. W. Mak, Organometallics 1999, 18, 3623.
20. L. X. Dai, T. Tu, S. L. You, W. P. Deng, X. L. Hou, Acc. Chem. Res. 2003, 36, 659.
21. A. Moyano, M. Rosol, R. M. Moreno, C. Lõpez, M. Maestro, Angew. Chem. 2005, 117, 1899
22. Angew. Chem. Int. Ed. 2005, 44, 1865.
23. L. Z. Du, J. F. Gong, C. Xu, Y. Zhu, Y. J. Wu, M. P. Song, Inorg. Chem. Commun. 2006, 9, 410.
24. V. A. Stepanova, V. V. Dunina, I. P. Smoliakova, Organometallics 2009, 28, 6546.
25. S. Kitagawa, R. Kitaura, S. Noro, Angew. Chem. 2004, 116, 2388
26. Angew. Chem. Int. Ed. 2004, 43, 2334.
27. S. R. Halper, L. Do, J. R. Stork, S. M. Cohen, J. Am. Chem. Soc. 2006, 128, 15255.
28. J. C. Garrison, M. J. Panzner, P. D. Custer, D. V. Reddy, P. L. Rinaldi, C. A. Tessier, W. J. Youngs, Chem. Commun. 2006, 4644.
29. H. B. Wu, Q. M. Wang, Angew. Chem. 2009, 121, 7479
30. Angew. Chem. Int. Ed. 2009, 48, 7343.
31. D. Rios, M. M. Olmstead, A. L. Balch, Inorg. Chem. 2009, 48, 5279.
32. Y. H. Sun, X. H. Zhu, Z. Chen, Y. Zhang, Y. Cao, J. Org. Chem. 2006, 71, 6281.
33. V. L. Whittle, J. A. G. Williams, Inorg. Chem. 2008, 47, 6596.
34. J. F. Gong, Y. H. Zhang, M. P. Song, C. Xu, Organometallics 2007, 26, 6487.
35. C. Xu, Y. P. Zhang, Z. Q. Wang, T. Liang, W. J. Fu, X. Q. Hao, Y. Xu, B. M. Ji, Inorg. Chim. Acta 2011, 365, 469.
36. C. Xu, Z. Q. Wang, X. M. Dong, X. Q. Hao, X. M. Zhao, B. M. Ji, M. P. Song, Inorg. Chim. Acta 2011, 373, 306.
37. C. Xu, Y. P. Zhang, Z. Q. Wang, W. J. Fu, X. Q. Hao, Y. Xu, B. M. Ji, Chem. Commun. 2010, 46, 6852.
38. C. Xu, J. F. Gong, Y. H. Zhang, Y. Zhu, Y. J. Wu, Aust. J. Chem. 2007, 60, 190.
39. C. Xu, J. F. Gong, G. Tao, Y. H. Zhang, Y. J. Wu, J. Mol. Catal. A 2008, 279, 69.
40. C. Xu, Y. X. Lu, X. H. Lou, Z. Q. Wang, W. J. Fu, B. M. Ji, Trans. Met. Chem. 2011, 36, 637.
41. G. R. Ren, X. L. Cui, E. B. Yang, F. Yang, Y. J. Wu, Tetrahedron 2010, 66, 4022.
42. L. H. Wang, J. Y. Li, X. L. Cui, Y. S. Wu, Z. W. Zhu, Y. J. Wu, Adv. Synth. Catal. 2010, 352, 2002.
43. R. B. Bedford, C. S. J. Cazin, M. B. Hursthouse, M. E. Light, K. J. Pike, S. Wimperis, J. Organomet. Chem. 2001, 633, 173.
44. R. B. Bedford, C. S. J. Cazin, S. J. Coles, T. Gelbrich, P. N. Horton, M. B. Hursthouse, M. E. Light, Organometallics 2003, 22, 987.
45. J. H. Chu, C. C. Chen, M. J. Wu, Organometallics 2008, 27, 5174.
46. A. A. Fuller, H. R. Hester, E. V. Salo, E. P. Stevens, Tetrahedron Lett. 2003, 44, 2935.
47. K. L. Billingsley, S. L. Buchwald, Angew. Chem. 2008, 120, 4773
48. Angew. Chem. Int. Ed. 2008, 47, 4695.
49. C. Xu, J. F. Gong, M. P. Song, Y. J. Wu, Trans. Met. Chem. 2009, 34, 179.
50. T. Ishiyama, K. Ishida, N. Miyaura, Tetrahedron 2001, 57, 9813.
51. A. Furstner, G. Seidel, Org. Lett. 2002, 4, 541.
52. K. L. Billingsley, T. E. Barder, S. L. Buchwald, Angew. Chem. 2007, 119, 5455
53. Angew. Chem. Int. Ed. 2007, 46, 5359.
54. K. C. Lam, T. B. Marder, Z. Y. Lin, Organometallics 2010, 29, 1849.
55. N. Kudo, M. Perseghini, G. C. Fu, Angew. Chem. 2006, 118, 1304
56. Angew. Chem. Int. Ed. 2006, 45, 1282.
57. K. L. Billingsley, K. W. Anderson, S. L. Buchwald, Angew. Chem. 2006, 118, 3564
58. Angew. Chem. Int. Ed. 2006, 45, 3484.
59. K. Billingsley, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 3358.
60. For reviews, see
61. B. Schlummer, U. Scholz, Adv. Synth. Catal. 2004, 346, 1599.
62. S. L. Buchwald, C. Mauger, G. Mignani, U. Scholz, Adv. Synth. Catal. 2006, 348, 23.
63. J. F. Hartwig, Synlett 2006, 1283.
64. J. F. Hartwig, Acc. Chem. Res. 2008, 41, 1534.
65. M. Beller, C. Breindl, T. H. Riermeier, A. Tillack, J. Org. Chem. 2001, 66, 1403.
66. H. V. R. Dias, W. Jin, Tetrahedron Lett. 1994, 35, 1365.
67. X. M. Zhang, B. Liu, A. L. Liu, W. L. Xie, W. Z. Chen, Organometallics 2009, 28, 1336.
68. R. B. Bedford, C. S. J. Cazin, D. Holder, Coord. Chem. Rev. 2004, 248, 2283.
69. T. Kinzel, Y. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2010, 132, 14073.
70. B. P. Fors, S. L. Buchwald, J. Am. Chem. Soc. 2010, 132, 15914.
71. C. S. Consorti, G. Ebeling, F. Rodembusch, V. Stefani, P. R. Livotto, F. Rominger, F. H. Quina, C. Yihwa, J. Dupont, Inorg. Chem. 2004, 43, 530.
72. S. Würtz, F. Glorius, Acc. Chem. Res. 2008, 41, 1523.
73. J. M. Antelo, L. Adrio, M. T. Pereira, J. M. Ortigueira, J. J. Fernández, J. M. Vila, Cryst. Growth Des. 2010, 10, 700.
74. J. M. Antelo, L. Adrio, M. T. Pereira, J. M. Ortigueira, A. Fernández, J. M. Vila, Eur. J. Inorg. Chem. 2011, 368.
75. C. Janiak, J. Chem. Soc., Dalton Trans. 2000, 3885.
76. S. M. Malathy Sony, M. N. Ponnuswamy, Cryst. Growth Des. 2006, 6, 736.
77. C. B. Aakeröy, T. A. Evans, K. R. Seddon, I. Pálinkõ, New J. Chem. 1999, 23, 145.
78. L. Brammer, E. A. Bruton, P. Sherwood, Cryst. Growth Des. 2001, 1, 277.
79. J. C. M. Rivas, L. Brammer, Inorg. Chem. 1998, 37, 4756.
80. T. Steiner, Angew. Chem. 2002, 114, 50
81. Angew. Chem. Int. Ed. 2002, 41, 48.
82. J. Albert, L. DâAndrea, J. Granell, R. Tavera, M. Font-Bardia, X. Solans, J. Organomet. Chem. 2007, 692, 3070.
83. N. N. L. Madhavi, A. K. Katz, H. L. Carrell, A. Nangia, G. R. Desiraju, Chem. Commun. 1997, 1953.
84. M. Nishio, CrystEngComm 2004, 6, 130.
85. W. Zhang, X. Tang, H. Ma, W. Sun, C. Janiak, Eur. J. Inorg. Chem. 2008, 2830.
86. M. Rausch, M. Vogel, H. Rosenberg, J. Org. Chem. 1957, 22, 900.
87. G. M. Sheldrick, SHELXL-97, Program for refinement of crystal structure, University of Göttingen, Germany, 1997.