Novel thiophene-based cycloruthenated compounds: Synthesis, characterization, and reactivity

Inorganic Chemistry

Volumn 50, Issue 1, 2011, Pages 37-45

  Cuesta, Luciano ^a   Maluenda, Irene ^a   Soler, Tatiana ^b   Navarro, Rafael ^a   Urriolabeitia, Esteban P ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

^b UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78650690840     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic101946n     Document Type: Article

References (81)

1. Albrecht, M. Chem. Rev. 2010, 110, 576 and references cited therein
2. Selected examples: Pfeffer, M. Pure. Appl. Chem. 1992, 64, 335
3. Dupont, J., Pfeffer, M., and Spencer, J. Eur. J. Inorg. Chem. 2001, 1917
4. Omae, I. Coord. Chem. Rev. 2004, 248, 995
5. Beletskaya, I. P. and Cheprakov, A. V. J. Organomet. Chem. 2004, 689, 4055
6. Omae, I. J. Organomet. Chem. 2007, 692, 2608
7. Selander, N. and Szabo, K. J. Dalton Trans. 2009, 627
8. Lyons, T. W. and Sanford, M. S. Chem. Rev. 2010, 110, 1147
9. Albrecht, M. and van Koten, G. Adv. Mater. 1999, 11, 171
10. Zhao, Q., Cao, T., Li, F., Li, X., Jing, H., Yi, T., and Huang, C. Organometallics 2007, 26, 2077
11. Bedford, R. B., Bethan, M., Butts, C. P., Coles, S. J., Hursthouse, M. B., Scully, P. N., Tucker, J. H. R., Wilkie, J., and Willener, Y. Chem. Commun. 2008, 2429
12. Wade, C. R. and Gabai, F. P. Inorg. Chem. 2010, 49, 714
13. Sylla, P., Sirlin, C., and Pfeffer, M. New J. Chem. 2010, 34, 762
14. Hudson, S. A. and Maitlis, P. M. Chem. Rev. 1993, 93, 861
15. Bruce, D. W., Deschenaux, R., Donnio, B., and Guillon, D. In Comprehensive Organometallic Chemistry III; Mingos, D. M. P. and Crabtree, R. H., Eds.; Elsevier: Amsterdam, The Netherlands, 2002; Vol. 12, p 217.
16. Severin, K., Bergs, R., and Beck, W. Angew. Chem., Int. Ed. 1998, 37, 1634
17. Dyson, P. J. and Sava, G. Dalton. Trans. 2006, 1929
18. Kurzeev, S. A., Vilesov, A. S., Fedorova, T. V., Stepanova, E. V., Koroleva, O. V., Bukh, C., Bjerum, M. J., Kurnikov, I. V., and Ryabov, A. D. Biochemistry 2009, 48, 4519
19. Pfeffer, M. and Dupont, J. Palladacycles, Synthesis, Characterization and Applications; Wiley-VCH: Weinheim, Germany, 2008.
20. Djukic, J. P., Sortais, J. B., Barloy, L., and Pfeffer, M. Eur. J. Inorg. Chem. 2009, 817
21. Bessho, T., Yoneda, E., Yum, J.-H., Guglielmi, M., Tavernelli, I., Imai, H., Rothlisberger, U., Nazeeruddin, M. K., and Grätzel, M. J. Am. Chem. Soc. 2009, 131, 5930
22. Bomben, P. G., Robson, K. C. D., Sedach, P. A., and Berlinguette, C. P. Inorg. Chem. 2009, 48, 9631
23. Koivisto, B. D., Robson, K. C. D., and Berlinguette, C. P. Inorg. Chem. 2009, 48, 9644
24. Ryabov, A. D., Sukharev, V. S., Alexandrova, L., Lagadec, R. L., and Pfeffer, M. Inorg. Chem. 2001, 40, 6529
25. Alpeeva, I. S., Soukharev, V. S., Alexandrova, L., Shilova, N. V., Bovin, N. V., Csöregi, E., Ryabov, A. D., and Sakharov, I. Y. J. Biol. Inorg. Chem. 2003, 8, 683
26. Soukharev, V. S., Ryabov, A. D., and Csöregi, E. J. Organomet. Chem. 2003, 668, 75
27. Lagadec, R. L., Rubio, L., Alexandrova, L., Toscano, R. A., Ivanova, E. V., Meskys, R., Laurinavivious, V., Pfeffer, M., and Ryabov, A. D. J. Organomet. Chem. 2004, 689, 4820
28. Ryabov, A. D., Lagadec, R. L., Estevez, H., Toscano, R. A., Hernandez, S., Alexandrova, L., Kurova, V. S., Fischer, A., Sirlin, C., and Pfeffer, M. Inorg. Chem. 2005, 44, 1626
29. Ryabov, A. D., Kurova, V. S., Ivanova, E. V., Lagadec, R. L., and Alexandrova, L. Anal. Chem. 2005, 77, 1132
30. Lagadec, R. L., Alexandrova, L., Estevez, H., Pfeffer, M., Razumiene, J., Laurinavivious, V., and Ryabov, A. D. Eur. J. Inorg. Chem. 2006, 2735
31. Gaidon, C., Jeannequin, P., Bischoff, P., Pfeffer, M., Sirlin, C., and Loeffler, J. P. J. Pharmacol. Exp. Ther. 2005, 315, 1403
32. Leyva, L., Sirlin, C., Rubio, L., Franco, C., Lagadec, R. L., Spencer, J., Bischoff, P., Gaidon, J., Loeffler, C. P., and Pfeffer, M. Eur. J. Inorg. Chem. 2007, 3055.
33. Leyva, L., Malek, F., Benzima, S., Denis, J. M., Gueulette, J., Dufour, P., Gaiddon, C., Loeffler, J. P., Sirlin, C., Pfeffer, M., and Bischoff, P. Lett. Drug Des. Discovery 2008, 5, 1
34. Meng, X., Leyva, M. L., Jenny, M., Gross, I., Benosman, S., Fricker, B., Harlepp, S., Hebraud, P., Boss, A., Wlosik, P., Bischoff, P., Sirlin, C., Pfeffer, M., Loeffler, J. P., and Gaiddon, C. Cancer Res. 2009, 69, 5458
35. Ruiz, J., Vicente, C., de Haro, C., and Bautista, D. Dalton Trans. 2009, 5071 For excellent reviews including noncyclometalated ruthenium complexes with anticancer properties, see: Dyson, P. J. and Sava, G. Dalton Trans. 2006, 1929
36. Ronconi, L. and Sadler, P. J. Coord. Chem. Rev. 2007, 251, 1633
37. Dani, P., Karlen, T., Gossage, R. A., Gladiali, S., and Van Koten, G. Angew. Chem., Int. Ed. 2000, 39, 743
38. Baratta, W., Da Ros, P., del Zotto, A., Sechi, A., Zangrando, E., and Rigo, P. Angew. Chem., Int. Ed. 2004, 43, 3584
39. Deeming, A. J., Jayasuriya, S. N., Arce, A. J., and Sanctis, Y. D. Organometallics 1996, 15, 786
40. Moorlag, C., Clot, O., Wolf, M. O., and Patrick, B. O. Chem. Commun. 2002, 3028
41. Koizumi, T., Tomon, T., and Kanata, K. Organometallics 2003, 22, 970
42. Koizumi, T., Tomon, T., and Kanata, K. J. Organomet. Chem. 2005, 690, 4272
43. Moorlag, C., Wolf, M. O., Bohne, C., and Patrick, B. O. J. Am. Chem. Soc. 2005, 127, 6382
44. Patra, S. K. and Bera, J. K. Organometallics 2006, 25, 6054
45. Lobana, T. S., Bawa, G., Castineiras, A., Butcher, R. J., and Zeller, M. Organometallics 2008, 27, 175
46. For an excellent overview of recent research on thiopene-based materials, see: Barbarella, G., Melucci, M., and Sotgiu, G. Adv. Mater. 2005, 17, 1581
47. Synthesis of the imines. 1a: Mendez, L. Y. V. and Koutnetzov, V. V. J. Heterocycl. Chem. 2008, 51, 6531 1b: Powell, A. B., Brown, R. J., Vavosudevan, K. V., and Cowley, A. H. Dalton Trans. 2009, 2521 1c: Hwang, W.-S., Wang, D.-L., and Chiang, M. Y. J. Organomet. Chem. 2000, 613, 231 1f: Joly, G. D. and Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 4102 1g: Cremonesi, G., Croce, P. D., Fontana, F., and La Rosa, C. Tetrahedron: Asymmetry 2008, 19, 554 1h: Tzeng, Y.-F., Wu, C.-Y., Hwang, W. S., and Hung, C.-H. J. Organomet. Chem. 2003, 687, 16 1i: Morimoto, T. and Sekiya, M. Chem. Lett. 1985, 9, 1731 1j: Macias, A., García, C., De Blas, A., Rodriguez, T., Bastida, R., and Souza, A. An. Quim. 1992, 88, 337 1k: Imhof, W. J. Organomet. Chem. 1997, 533, 31 1l: Anderson, C., Crespo, M., Font-Bardía, M., Klein, A., and Solans, X. J. Organomet. Chem. 2000, 601, 22 1o: Sone, T. Bull. Chem. Soc. Jpn. 1964, 37, 1197 1q: Audoye, P., Coumes, R.-C., Gaset, A., and Gorrichon, J.-P. Can. J. Chem. 1982, 60, 1148
48. Fernández, S., Pfeffer, M., Ritleng, V., and Sirlin, C. Organometallics 1999, 18, 2390
49. Recent example not included in ref 7: Djukic, J.-P., Fetzer, L., Czysz, A., Iali, W., Sirlin, C., and Pfeffer, M. Organometallics 2010, 29, 1675
50. 7 times faster than does benzene. See: Swanston, J. Thiophene. Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim, Germany, 2006. For an overview of electrophilic substitutions of five-menbered rings, see
51. Merino, G. Adv. Heterocycl. Chem. 1975, 13, 235
52. Albert, J., Ceder, R. M., Gómez, M., Granell, J., and Sales, J. Organometallics 1992, 11, 1536
53. De Munno, G., Ghedini, M., and Neve, F. Inorg. Chim. Acta 1995, 239, 155
54. Albert, J., Granell, J., Sales, J., Font-Bardía, M., and Solans, X. Organometallics 1995, 14, 1393
55. Gómez, M., Granell, J., and Martínez, M. Organometallics 1997, 16, 2539
56. Gómez, M., Granell, J., and Martínez, M. J. Chem. Soc., Dalton Trans. 1998, 37.
57. Gómez, M., Granell, J., and Martínez, M. Eur. J. Inorg. Chem. 2000, 217
58. Gorunova, O. N., Keuseman, K. J., Goebel, B. M., Kataeva, N. A., Churakov, A. V., Kuz'mina, L. G., Dunina, V. V., and Smoliakova, I. P. J. Organomet. Chem. 2004, 689, 2382
59. Keuseman, K. J., Smoliakova, I. P., and Dunina, V. V. Organometallics 2005, 24, 4159
60. Bielsa, R., Larrea, A., Navarro, R., Soler, T., and Urriolabeitia, E. P. Eur. J. Inorg. Chem. 2005, 1724
61. Mawo, R. Y., Mustakim, S., Young, V. G., Jr., Hoffmann, M. R., and Smoliakova, I. P. Organometallics 2007, 26, 1801
62. Aguilar, D., Aragüés, M. A., Bielsa, R., Serrano, E., Navarro, R., and Urriolabeitia, E. P. Organometallics 2007, 26, 3541
63. Aguilar, D., Aragüés, M. A., Bielsa, R., Serrano, E., Soler, T., Navarro, R., and Urriolabeitia, E. P. J. Organomet. Chem. 2008, 693, 417
64. Bielsa, R., Navarro, R., Soler, T., and Urriolabeitia, E. P. Dalton Trans. 2008, 1203
65. Bielsa, R., Navarro, R., Soler, T., and Urriolabeitia, E. P. Dalton Trans. 2008, 1787
66. Bielsa, R., Navarro, R., Urriolabeitia, E. P., and Lledós, A. Inorg. Chem. 2007, 46, 10133
67. Aguilar, D., Bielsa, R., Contel, M., Lledós, A., Navarro, R., Soler, T., and Urriolabeitia, E. P. Organometallics 2008, 27, 2929
68. Katritzky, A. R. and Taylor, R. Electrophilic Substitution of Heterocycles, Quantitative Aspects, Advances in Heterocyclic Chemistry Series; Academic Press: San Diego, CA, 1990; Vol. 47.
69. Taylor, R. Electrophilic Aromatic Substitution; Wiley: New York, 1990.
70. De La Mare, P. B. Electrophilic Halogenation; Cambridge University Press: Cambridge, U.K., 1976; Chapter 5.
71. Kalyani, D., Dick, R. A., Anani, Q. W., and Sanford, M. S. Tetrahedron 2006, 62, 11483
72. See ref 2g.
73. Giri, R., Chen, X., and Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 2112
74. Synthesis of 3-iodo-2-formylthiophene (3a): Antonioletti, R., D'Auria, M., D'Onofrio, F., Piancatelli, G., and Scettri, A. J. Chem. Soc., Perkin Trans. 1 1986, 1755
75. Guillard, R., Fournari, P., and Person, M. Bull. Soc. Chim. Fr. 1967, 4121
76. Sonoda, M., Kinoshita, S., Lu, T., Fukuda, H., Miki, K., Umeda, R., and Tobe, Y. Synth. Commun. 2009, 39, 3315 Synthesis of 2-iodo-3-formylthiophene (3n): Wunderlich, S. H. and Knochel, P. Angew. Chem., Int. Ed. 2007, 46, 7685 Synthesis of 2-iodo-3-formylthiophene (3k): Gronomitz, S. and Dahlgren, T. Chem. Scr. 1977, 12, 57
77. Prestch, E., Bühlman, P., Affolter, C., Herrera, A., and Martínez, R. Structural Determination of Organic Compounds; Springer-Verlag Ibérica: Barcelona, Spain, 2001.
78. CrysAlis RED, version 1.171.27p8; Oxford Diffraction Ltd.: Oxford, U.K., 2005.
79. Sheldrick, G. M. SADABS: Empirical absorption correction program; Göttingen University: Göttingen, Germany, 1996.
80. SHELXS-86: Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467.
81. SHELXL-97: Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112.