Crown ether palladacycles as metalloligands: Suitable precursors for tetranuclear mixed transition/non-transition metal complexes

Organometallics

Volumn 28, Issue 23, 2009, Pages 6657-6665

  Castro Juiz, Samuel ^a   Fernández, Alberto ^a   López Torres, Margarita ^a   Vázquez García, Digna ^a   Suárez, Antonio J ^a   Vila, José M ^b   Fernández, Jesús J ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

C-H ACTIVATION; CHLORIDE LIGANDS; METALLOLIGANDS; METATHESIS REACTIONS; PALLADACYCLES; SCHIFF-BASE LIGANDS; TETRABUTYL-AMMONIUM CHLORIDE; X-RAY SINGLE-CRYSTAL DIFFRACTION;

BARIUM; BARIUM COMPOUNDS; CHLORINE COMPOUNDS; CROWN ETHERS; ETHERS; FLUORINE CONTAINING POLYMERS; FUNCTIONAL GROUPS; METAL COMPLEXES; ORGANOMETALLICS; PALLADIUM; PALLADIUM COMPOUNDS; POSITIVE IONS; TRANSITION METAL COMPOUNDS; TRANSITION METALS; X RAY DIFFRACTION ANALYSIS;

LIGANDS;

EID: 71949121965     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900390a     Document Type: Article

References (97)

1. (a) Izatt, R. M.; Bradshaw, J. S.; Nielsen, S. A.; Lamb, J. D.; Christensen, J. J.; Sen, D. Chem. Rev. 1985, 85,271.
2. (b) Inoue, Y.; Gokel G. W., Eds. Cation Binding by Macrocycles; Marcel Dekker: New York, 1990.
3. (a) Lehn, J. M.; Montavon, F. Helv. Chim. Acta 1978, 61, 67.
4. (b) Izatt, R. M. Christensen, J. J., Eds. Synthetic Multidentate Macrocyclic Compounds; Academic Press: London, 1978.
5. (c) Vögtle, F.; Weber, E., Eds.; Host-/Guest Complex Chemistry: Macrocycles; Springer-Verlag: Berlin, 1985.
6. (d) Izatt, R. M.; Christensen, J. J., Eds. Synthesis of Macrocycles: The Design of Selective Complexing Agents. In Progress in Macrocyclic Chemistry, Vol. 3; Wiley: New York, 1987.
7. (e) Gokel, G. W. Crown Ethers and Cryptands. In Monographs in Supramolecular Chemistry; The Royal Society of Chemistry: Cambridge, 1991.
8. (f) Cooper, S. R., Ed. Crown Compounds: towards Future Applications,; Wiley Interscience: New York, 1992.
9. (g) Yordanov, A. T.; Roundhill, D. M. Coord. Chem. Rev. 1998, 170, 93.
10. (a) Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 2495.
11. (b) Pedersen, C. J. Science 1988, 241, 536.
12. (c) Steed, J. W. Coord. Chem. Rev. 2001, 215, 171.
13. (a) Xiaotian, Q.; Zaide, Z.; Minggui, X.; Yongchang, Z.; Ying, T. Talanta 1998,46,45.
14. (b) Rosa, D. T.; Young, V. G; Coucouvanis, D. Inorg. Chem. 1998,37, 5042.
15. (c) Dillon, R. E. A.; Stem, C. L.; Shriver, D. F. Solid State Ionics 2000, 133, 247.
16. (d) Yam, V. W. W.; Tang, R. P. L.; Wong, K. M. C.; Lu, X. X.; Cheung, K. K.; Zhu, N. Chem.-Eur. J. 2002, 8, 4066.
17. (e) Breccia, P.; Van Gool, M.; Pérez-Fernández, R.; Martín-Santamaría, S.; Gago, F.; Prados, P.; de Mendoza, J. J. Am. Chem. Soc. 2003, 125, 8270.
18. (f) Siu, P. K. M.; Lai, S. W; Lu, W; Zhu, N.; Che, C. M. Eur. J. Inorg. Chem. 2003, 2749.
19. (a) Ohshita, J.; Uemura, T.; Inoue, T.; Hino, K.; Kunai, A. Organometallics 2006, 25, 2225.
20. (b) Liu, W; Chen, Y.; Wang, R.; Zhou, X. H.; Zuo, J. L.; You, X. Z. Organometallics 2008,27,2990.
21. (c) Perekalin, D. S.; Babak, M. V.; Novikov, V. V.; Petrovskii, P. V.; Lyssenko, K. A.; Corsini, M.; Zanello, P.; Kudinov, A. R. Organometallics 2008, 27, 3654.
22. Kelly, M. E.; Dietrich, A.; Gomez-Ruiz, S.; Kalinowski, B.; Kaluderovic, G. N.; Muller, T.; Paschke, R.; Schmidt, J.; Steinborn, D.; Wagner, C.; Schmidt, H. Organometallics 2008, 27,4917.
23. (a) Lehn, J. M. Supramolecular Chemistry, Concepts and Perspectives; VCH: Weinheim, 1995.
24. (b) Nabeshima, T. Coord. Chem. Rev. 1996, 148,151.
25. (c) Nabeshima, T.; Akine, S.; Saiki, T. Rev. Heteroat. Chem. 2000, 22, 219.
26. (d) Albrecht, M. Chem. Rev. 2001,101, 3457.
27. Kleinmann, J. P.; Dubeck, M. J. Am. Chem. Soc. 1963, 86,1544.
28. (a) Dehand, J.; Pfeffer, M. Coord. Chem. Rev. 1976, 18, 327.
29. (b) Bruce, M. I. Angew. Chem., Int. Ed. Engl. 1977,16, 73.
30. (c) Omae, I. Coord. Chem. Rev. 1982,42,245.
31. (d) Constable, E. C. Polyhedron 1984, 3, 1037.
32. (e) Rothwell, I. P. Polyhedron 1985,4, 177.
33. (f) Wu, Y.; Huo, S.; Gong, J.; Cui, X.; Ding, L.; Ding, K.; Du, C.; Liu, Y.; Song, M. J. Organomet. Chem. 2001,637-639,27.
34. (g) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750.
35. (h) Omae, I. Coord. Chem., Rev. 2004, 248, 995.
36. (i) Mohr, F.; Priver, S. H.; Bhargava, S. K.; Bennett, M. A. Coord. Chem. Rev. 2006, 250, 1851.
37. (a) Marcos, M. In Metallomesogens. Synthesis, Properties and Applications; Serrano, J. L., Ed.; VCH: Weinheim, 1996.
38. (b) Wild, S. B. Coord. Chem. Rev. 1997, 166, 291.
39. (c) Gómez-Quiroga, A.; NavarroRanninger, C. Coord. Chem. Rev. 2004, 248, 119.
40. (d) Slagt, M. Q.; van Zwieten, D. A. P.; Moerkerk, A. J. C. M.; Klein Gebbink, R. J. M.; van Koten, G. Coord. Chem. Rev. 2004, 248, 2275.
41. (e) Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527.
42. (f) Ghedini, M.; Aiello, L; Crispini, A.; Golemme, A.; La Deda, M.; Pucci, D. Coord. Chem. Rev. 2006, 250, 1373.
43. (g) Gagliardo, M.; Rodríguez, G; Dam, H. H.; Lutz, M.; Spek, A. L.; Havenith, R. W. A.; Coppo, P.; De Cola, L.; Hartl, F.; van Klink, G. P. M.; van Koten, G. Inorg. Chem. 2006, 45, 2143.
44. (h) Ruiz, J.; Lorenzo, J.; Sanglas, L.; Cutillas, N.; Vicente, C.; Villa, M. D.; Aviles, F. X; Lopez, G.; Moreno, V.; Pérez, J.; Bautista, D. Inorg. Chem. 2006, 45, 6347.
45. (i) Pucci, D.; Bameiro, G.; Bellusci, A.; Crispini, A.; Ghedini, M. J. Organomet. Chem. 2006,691,1138.
46. (j) Kui, S. C. F.; Sham, I. H. T.; Cheung, C. C. C.; Ma, C.-W.; Pan, B.; Zhu, N.; Che, C. M.; Fu, W.-F. Chem.-Eur. J. 2007, 13, 417.
47. (k) Johansson,R.; Wendt, O. L. Dalton Trans. 2007,488.
48. (l) Tang, L.;Zhang, Y; Ding, L.; Li, Y.; Mok, K-F.; Yeo, W.-C.; Leung, P.-H. Tetrahedron Lett. 2007, 48, 33.
49. (m) Dupont, J.; Pfeffer, M., Eds. Palladacycles; Wiley-VCH: Weinheim, 2008.
50. Armarego, W. L. F.; Chai, C. L. L. Purification of Laboratory Chemicals, 5th ed.; Butterworth-Heinemann: Bodmin, 2003.
51. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112.
52. (a) Vila, J. M.; Gayoso, M.; Pereira, M. T.; López, M.; Alonso, G.; Fernández, J. J. J. Organomet. Chem. 1993, 445, 287.
53. (b) Dotta, P.; Kumar, P. G. A.; Pregosin, P. S.; Albinati, A.; Rizatto, S. Organometallics 2004, 23,4247.
54. Onoue, H.; Moritani, I. J. Organomet. Chem. 1972, 43,431.
55. Ustinyuk, Y. A.; Chertov, V. A.; Barinov, I. V. J. Organomet. Chem. 1971, 29, C53.
56. Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, 5th ed.; Wiley & Sons: New York, 1997.
57. (a) Navarro-Ranninger, C.; López-Solera, I.; González, V. M.; Pérez, J. M.; Alvarez-Valdés, A.; Martin, A.; Raithby, P. R.; Masaguer, J. R.; Alonso, C. Inorg. Chem. 1996, 35, 5181.
58. (b) Herrman, W A.; Brown, V P. M.; Reisinger, C P. J. Organomet. Chem. 1999, 576, 23.
59. (c) Mosteiro, R.; Perille, E.; Fernández, A.; López-Torres, M.; Vila, J. M.; Suárez, A.; Ortigueira, J. M.; Pereira, M. T.; Fernández, J. J. Appl. Organomet. Chem. 2000, 14, 634.
60. (d) Evans, P. G.; Brown, N. A.; Clarkson, G. J.; Newman, C. P.; Rourke, J. P. J. Organomet. Chem. 2006, 691, 1251.
61. Teijido, B.; Fernández, A.; López-Torres, M.; Suárez, A.; Vila, J. M.; Mosteiro, R.; Fernández, J. J. Organometallics 2002, 21, 1304.
62. (a) Tusek-Bozic, L.; Curie, M.; Traldi, P. Inorg. Chim. Acta 1997, 254,49.
63. (b) Tusek-Bozic, L.; Komac, M.; Curic, M.; Lycka, A.; Dálpaos, M.; Scarcia, V; Furlani, A. Polyhedron 2000, 19, 937.
64. Vila, J. M.; Gayoso, M.; Fernández, A.; Bailey, N. A.; Adams, H. J. Organomet. Chem. 1993, 448, 233.
65. (a) Vila, J. M.; Gayoso, M.; Pereira, M. T.; Ortigueira, J. M.; Fernández, A.; Bailey, N. A.; Adams, H. Polyhedron 1993, 12,171-180.
66. (b) Zhao, G.; Wang, Q. G.; Mak, T. C. W. J. Chem. Soc., Dalton Trans. 1998, 1241.
67. (a) Gokel, G. W.; Leevy, W. M.; Weber, M. E. Chem. Rev. 2004, 104, 2723.
68. (b) Brown, M. D.; Dyke, J. M.; Ferrante, F.; Levason, W.; Ogden, J. S.; Webster, M. Chem.-Eur. J. 2006,12, 2620.
69. Arias, J.; Bardaji, M.; Espinet, P. J. Organomet. Chem. 2006, 691, 4990.
70. Owen, J. D. Dalton Trans. 1981,1066, and references therein.
71. Baylies, C. J.; Harding, L. P.; Jeffery, J. C.; Riis-Johannessen, T.; Rice, C. R. Angew. Chem., Int. Ed. 2004, 43,4515.
72. (a) Takeda, Y.; Yano, H.; Ishibashi, M.; Isozumo, H. Bull. Chem. Soc. Jpn. 1980, 53, 72.
73. (b) Koritsanszky, T.; Buschmann, J.; Luger, P.; Knöchel, A.; Patz, M. J. Am. Chem. Soc. 1994, 116, 6748.
74. (c) Kuate, A. C. T.; Reeske, G; Schurmann, M.; Costisella, B.; Jurkschat, K. Organometallics 2008, 27, 5577.
75. (d) Coronado, E.; Galan-Mascaros, J. R.; MartGastaldo, C.; Waerenborgh, J. C.; Gaczynski, P. Inorg. Chem. 2008, 47, 6829.
76. (e) Coco, S.; Cordovilla, C.; Espinet, P.; Gallani, J. L.; Guillon, D.; Donnio, B. Eur. J. Inorg. Chem. 2008, 1210.
77. (a) Yam, V. W.; Tang, R. P.; Wong, K. M.; Ko, C.; Cheung, K. Inorg. Chem. 2001,40,571.
78. (b) Sureshan, K M.; Shashidhar, M. S.; Varma, A. J. J. Org. Chem. 2002, 67, 6884.
79. (a) Nelsen, D. L.; White, P. S.; Gagne, M. R. Organometallics 2005, 24, 5419.
80. (b) Endicott, C.; Strauss, H. L. J. Phys. Chem. A 2007, 111, 1236.
81. Nazarenko, A. Y.; Rusanov, E. B. J. Coord. Chem. 1995, 34, 265.
82. Metz, B.; Weiss, R. Acta Crystallogr. Sect. B 1973, 29, 1088.
83. Nazarenko, A. Y.; Rusanov, E. B. Polyhedron 1994,13, 2549.
84. Costero, A. M.; Villarroya, J. P.; Gil, S.; Aurell, M. J.; Ramirez de Arellano, M. C. Tetrahedron 2002, 58, 6724.
85. Nuss, H.; Jansen, M. Angew. Chem., Int. Ed. 2006, 45,4369.
86. (a)Vila, J. M.; Gayoso, M.; Pereira, M. T.; Romar, A.; Fernández, J. J.;Thronton-Pett, M. J. Organomet. Chem. 1991, 401, 385.
87. (b)NavarroRanninger, C.; López-Solera, I.; Alvarez-Valdes, A.; Rodríguez, J. H.; Masaguer, J. R.; García-Ruano, J. L. J. Organomet. Chem. 1994, 476, 19.
88. (c) Fernández, A.; Pereira, E.; Fernández, J. J.; López-Torres, M.; Suárez, A.; Mosteiro, R.; Pereira, M. T.; Vila, J. M. New J. Chem. 2002, 26, 895.
89. (d) Chen, Ch.L.; Liu, Y-H.; Peng, Sh.-M.; Liu, S.-T. J. Organomet. Chem. 2004, 689, 1806.
90. (a) Crispini, A.; De Munno, G.; Ghedini, M.; Neve, F. J. Organomet. Chem. 1992, 427, 409.
91. (b) Kleij, A. W; Kleijn, H.; Jastrzebski, J. T. B. H.; Spek, A. L.; van Koten, G. Organometallics 1999, 18,277.
92. (c) Kleij, A. W.; Gebbink, R. J. M. K.; van den Nieuwenhuijzen, P. A. J.; Kooijman, H.; Lutz, M.; Spek, A. L.; van Koten, G. Organometallics 2001, 20, 634.
93. (d) Kok-Peng, J.; Tan Liu, G-K.; Vittal, J. J.; Leung, P.-H. Inorg. Chem. 2003, 42, 7674.
94. (e) Naya, L.; Vázquez-García, D.; LópezTorres, M.; Fernández, A.; Vila, J. M.; Gómez-Blanco, N.; Fernández, J. J. J. Organomet. Chem. 2008, 693, 685.
95. (a) Navarro-Ranninger, C.; Zamora, F.; López-Solera, I.; Monge, A.; Masaguer, J. R. J. Organomet. Chem. 1996, 506, 149.
96. (b) Pereira, M. T.; Vila, J. M.; Gayoso, E.; Gayoso, M.; Hiller, W; Strähle, J. J. Coord. Chem. 1988, 18, 245.
97. (c) Teijido, B.; Fernández, A.; LópezTorres, M.; Castro-Juiz, S.; Suárez, A.; Ortigueira, J. M.; Vila, J. M.; Fernández, J. J. J. Organomet. Chem. 2000, 598, 71.