Octahedral RuII complexes with [PNO] hydrazonic ligands: Synthesis, structure, reactivity and catalytic activity in the addition of benzoic acid to alkynes

European Journal of Inorganic Chemistry

Volumn , Issue 12, 2006, Pages 2422-2436

  Pelagatti, Paolo ^a   Bacchi, Alessia ^a   Balordi, Marcella ^a   Bolaño, Sandra ^b,c   Calbiani, Francesca ^a   Elviri, Lisa ^a   Gonsalvi, Luca ^b   Pelizzi, Corrado ^a   Peruzzini, Maurizio ^b   Rogolino, Dominga ^a  

^a UNIVERSITY OF PARMA   (Italy)

^b ICCOM CNR   (Italy)

^c UNIVERSITY OF VIGO   (Spain)

Author keywords

Enol esters; Homogeneous catalysis; Mass spectrometry; Ruthenium; Tridentate ligands

Indexed keywords

BENZOIC ACID; CARBOXYLATION; CATALYSIS; CATALYST ACTIVITY; CHELATION; CHLORINE COMPOUNDS; ESTERS; HYDROCARBONS; LIGANDS; RUTHENIUM COMPOUNDS; SINGLE CRYSTALS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

BIS-CHELATE COMPLEXES; ENOL ESTERS; EXPERIMENTAL CONDITIONS; HOMOGENEOUS CATALYSIS; OXYGEN TRANSFER; P-CYMENE; RUTHENIUM PRECURSORS; STRUCTURE REACTIVITY; SYNTHESISED; TRIDENTATE LIGANDS;

MASS SPECTROMETRY;

EID: 33745647597     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200600016     Document Type: Article

References (84)

1. a) M. Alvarez, N. Lugan, R. Mathieu, J. Chem. Soc., Dalton Trans. 1994, 2755-2760;
2. b) J. R. Dilworth, S. D. Howe, A. J. Hutson, J. R. Miller, J. Silver, R. M. Thompson, M. Harman, M. B. Hursthouse, J. Chem. Soc., Dalton Trans. 1994, 3553-3562;
3. c) K. K. Hii, S. D. Perera, B. L. Shaw, J. Chem. Soc., Dalton Trans. 1994, 3589-3596;
4. d) P. Bhattacharyya, J. Parr, A. M. Z. Slawin, J. Chem. Soc., Dalton Trans. 1998, 3609-3614;
5. e) P. Bhattacharyya, M. L. Loza, J. Parr, A. M. Z. Slawin, J. Chem. Soc., Dalton Trans. 1999, 2917-2921;
6. f) J. D. G. Correia, A. Domingos, A. Paulo, I. Santos, J. Chem. Soc., Dalton Trans. 2000, 2477-2482;
7. g) J. W. Faller, G. Mason, J. Parr, J. Organomet. Chem. 2001, 626, 181-185;
8. h) K. Nakajima, S. Ishibashi, M. Inamo, M. Kojima, Inorg. Chim. Acta 2001, 325, 36-44;
9. i) G. Sanchez, F. Momblona, J. L. Serrano, L. Garcia, E. Perez, J. Perez, G. Lopez, J. Coord. Chem. 2002, 55, 917-923;
10. j) M. Ahmad, S. D. Perera, B. L. Shaw, M. Thornton-Pett, J. Chem. Soc., Dalton Trans. 2002, 1954-1962;
11. k) S. R. Korupoju, R.-Y. Lai, Y.-H. Liu, S.-M. Peng, S.-T. Liu, Inorg. Chim. Acta 2005, 358, 3003-3008.
12. a) H. Yang, M. Alvarez, N. Lugan, R. Mathieu, J. Chem. Soc., Chem. Commun. 1995, 1721-1722;
13. b) H. Yang, M. Alvarez-Gressier, N. Lugan, R. Mathieu, Organometallics 1997, 16, 1401-1409;
14. c) H. L. Kwong, W. S. Lee, T. S. Lai, W. T. Wong, Inorg. Chem. Commun. 1999, 2, 66-69;
15. d) H. Dai, X. Hu, H. Chen, C. Bai, Z. Zheng, Tetrahedron: Asymmetry 2003, 14, 1467-1472.
16. P. Pelagatti, A. Bacchi, M. Carcelli, M. Costa, A. Fochi, P. Ghidini, E. Leporati, M. Masi, C. Pelizzi, G. Pelizzi, J. Organomet. Chem. 1999, 583, 94-105.
17. a) A. Bacchi, M. Carcelli, M. Costa, P. Pelagatti, C. Pelizzi, G. Pelizzi, Gazz. Chim. Ital. 1994, 124, 429-435;
18. b) A. Bacchi, M. Carcelli, M. Costa, A. Leporati, E. Leporati, P. Pelagatti, C. Pelizzi, G. Pelizzi, J. Organomet. Chem. 1997, 535, 107-120.
19. a) P. Pelagatti, A. Bacchi, C. Bobbio, M. Carcelli, M. Costa, C. Pelizzi, C. Vivorio, Organometallics 2000, 19, 5440-5446;
20. b) P. Pelagatti, A. Bacchi, C. Bobbio, M. Carcelli, M. Costa, A. Fochi, C. Pelizzi, J. Chem. Soc., Dalton Trans. 2002, 1-7;
21. c) P. Pelagatti, A. Bacchi, M. Carcelli, M. Costa, H.-W. Frühauf, K. Goubitz, C. Pelizzi, M. Triclistri, K. Vrieze, Eur. J. Inorg. Chem. 2002, 439-446.
22. C. Bruneau, P. H. Dixneuf, Ruthenium Catalysts and Fine Chemistry, Springer GmbH, Berlin, Germany, 2004.
23. J. P. Monthéard, M. Camps, G. Seytre, J. Guillet, J. C. Dubois, Angew. Makromol. Chem. 1978, 72, 45-55.
24. E. Bruneau, M. Neveux, Z. Kabouche, C. Ruppin, P. H. Dixneuf, Synlett 1991, 755-763.
25. a) R. C. Cambie, R. C. Hayward, J. L. Jurlina, P. S. Rutledge, P. D. Woodgate, J. Chem. Soc., Perkin Trans. 1 1978, 126-130;
26. b) S. Torii, T. Inokuchi, S. Misima, T. Kobayashi, J. Org. Chem. 1980, 45, 2731-2735;
27. c) S. Stavber, B. Sket, B. Zajc, M. Zupan, Tetrahedron 1989, 45, 6003-6010;
28. d) A. D. Cort, J. Org. Chem. 1991, 56, 6708-6709.
29. a) A. Demonceau, E. Saive, Y. de Froidmont, A. F. Noels, A. J. Hubert, Tetrahedron Lett. 1992, 33, 2009-2012;
30. b) W. B. Motherwell, L. R. Roberts, J. Chem. Soc., Chem. Commun. 1992, 1582-1583.
31. a) L. F. Tietze, A. Montenbruck, C. Schneider, Synlett 1994, 509-510;
32. b) M. C. Pirrung, Y. R. Lee, Tetrahedron Lett. 1994, 35, 6231-6234.
33. K. E. Koenig, G. L. Bachman, B. E. Vineyard, J. Org. Chem. 1980, 45, 2362-2365.
34. a) N. Sakai, K. Nozaki, K. Massima, H. Takaya, Tetrahedron: Asymmetry 1992, 3, 583-586;
35. b) C. G. Arena, F. Nicolò, D. Drommi, G. Bruno, F. Faraone, J. Chem. Soc., Chem. Commun. 1994, 2251-2252.
36. M. Rotem, Y. Shvo, Organometallics 1983, 2, 1689-1691.
37. a) T. Mitsudo, Y. Hori, Y. Watanabe, J. Org. Chem. 1985, 50, 1566-1568;
38. b) T. Mitsudo, Y. Hori, Y. Yamakawa, Y. Watanabe, Tetrahedron Lett. 1986, 27, 2125-2126;
39. c) T. Mitsudo, Y. Hori, Y. Yamakawa, Y. Watanabe, J. Org. Chem. 1987, 52, 2230-2239.
40. a) C. Ruppin, P. H. Dixneuf, Tetrahedron Lett. 1986, 27, 6323-6324;
41. b) C. Ruppin, P. Dixneuf, Tetrahedron Lett. 1988, 29, 5365-5368;
42. c) H. Doucet, J. Höfer, C. Bruneau, P. H. Dixneuf, J. Chem. Soc., Chem. Commun. 1993, 850-851;
43. d) H. Doucet, B. Martin-Vaca, C. Bruneau, P. H. Dixneuf, J. Org. Chem. 1995, 60, 7247-7255;
44. e) H. Doucet, N. Derrien, Z. Kabouche, C. Bruneau, P. H. Dixneuf, J. Organomet. Chem. 1997, 551, 151-157.
45. a) T. Opstal, F. Verpoort, Tetrahedron Lett. 2002, 43, 9259-9263;
46. b) B. De Clercq, F. Verpoort, J. Organomet. Chem. 2003, 672, 11-16;
47. c) K. Melis, D. De Vos, P. Jacobs, F. Verpoort, J. Organomet. Chem. 2003, 671, 131-136;
48. d) K. Melis, F. Verpoort, J. Mol. Catal. A 2003, 194, 39-47.
49. L. J. Goossen, J. Paetzold, D. Koley, Chem. Commun. 2003, 706-707.
50. M. Neveux, B. Seller, F. Hagerdon, C. Bruneau, P. H. Dixneuf, J. Organomet. Chem. 1993, 451, 133-138.
51. a) K. Everaere, A. Mortreux, M. Bulliard, J. Brussee, A. van der Gen, G. Nowogroki, J.-F. Carpentier, Eur. J. Org. Chem. 2001, 275-291;
52. b) C. A. Sandoval, T. Ohkuma, K. Muñiz, R. Noyori, J. Am. Chem. Soc. 2003, 125, 13490-13503;
53. c) P. Pelagatti, M. Carcelli, F. Calbiani, C. Cassi, L. Elviri, C. Pelizzi, U. Rizzotti, D. Rogolino, Organometallics 2005, 24, 5836-5844.
54. D. Feichtinger, D. A. Plattner, Chem. Eur. J. 2001, 7, 591-599.
55. D. Feichtinger, D. A. Plattner, P. Chen, J. Am. Chem. Soc. 1998, 120, 7125-7126.
56. G. Gerdes, P. Chen, Organometallics 2004, 23, 3031-3036.
57. a) P. Crochet, J. Gimeno, S. Garcia-Granada, J. Borge, Organometallics 2001, 20, 4369-4377;
58. b) P. Crochet, J. Gimeno, J. Borge, S. García-Granada, New J. Chem. 2003, 27, 414-420.
59. S. M. O. Quintal, H. I. S. Nogueira, V. Félix, M. G. B. Drew, J. Chem. Soc., Dalton Trans. 2002, 4479-4487.
60. a) I. P. Evans, A. Spencer, G. Wilkinson, J. Chem. Soc., Dalton Trans. 1973, 204;
61. b) E. Alessio, G. Mestroni, G. Nardin, W. M. Attia, M. Calligaris, G. Sava, S. Zorzet, Inorg. Chem. 1988, 27, 4099-4106.
62. P. E. Garrou, Chem. Rev. 1981, 81, 229-266.
63. a) R. F. R. Jazzar, M. F. Mahon, M. K. Whittlesey, Organometallics 2001, 20, 3745-3751;
64. b) T. Suárez, B. Fontal, M. Reyes, F. Bellandi, R. R. Contreras, E. Millán, P. Cancines, D. Paredes, Transition Met. Chem. 2003, 28, 217-219.
65. V. Y. Kukushkin, Coord. Chem. Rev. 1995, 139, 375-407.
66. a) J. C. Bryan, R. E. Stenkamp, T. H. Tulip, J. M. Mayer, Inorg. Chem. 1987, 26, 2283-2288;
67. b) N. Koshino, J. H. Espenson, Inorg. Chem. 2003, 42, 5735-5742.
68. a) A. M. Khenkin, R. Neumann, J. Am. Chem. Soc. 2002, 124, 4198-4199;
69. b) F. J. Arnáiz, R. Aguado, M. R. Pedrosa, M. A. Maestro, Polyhedron 2004, 23, 537-543;
70. c) K. Most, S. Köpke, F. Dall'Antonia, N. C. Mösch-Zanetti, Chem. Commun. 2004, 1676-1677;
71. d) A. Lehtonen, R. Sillanpää, Polyhedron 2005, 24, 257-265.
72. J. P. McNamara, I. H. Hillier, T. S. Bhachu, C. D. Garner, Dalton Trans. 2005, 3572-3579.
73. J. S. Jaswal, S. J. Rettig, B. R. James, Can. J. Chem. 1990, 68, 1808-1817.
74. J. Höfer, H. Doucet, C. Bruneau, P. H. Dixneuf, Tetrahedron Lett. 1991, 32, 7409-7410.
75. P. S. Hallman, T. A. Stephenson, G. Wilkinson, Inorg. Synth. 1970, 12, 237-240.
76. a) SAINT: SAX, Area Detector Integration, Siemens Analytical instruments INC., Madison, Wisconsin, USA;
77. b) SADABS: Siemens Area Detector Absorption Correction Software, Sheldrick G., 1996, University of Goettingen, Germany;
78. c) SMART for WNT/2000 version 5.622, Smart Software Reference Manual; Bruker Advanced X-ray Solution, Inc.: Madison, WI, 2001.
79. A. Altomare, M. C. Burla, M. Cavalli, G. Cascarano, C. Giacovazzo, A. Gagliardi, A. G. Moliterni, G. Polidori, R. Spagna, Sir97: A New Program For Solving And Refining Crystal Structures, 1997, Istituto di Ricerca per lo Sviluppo di Metodologie Cristallografiche, CNR, Bari.
80. G. Sheldrick, Shelx197. Program for structure refinement. University of Göttingen, Germany, 1997.
81. L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837.
82. M. Nardelli, J. Appl. Crystallogr. 1995, 28, 659.
83. a) F. H. Allen, O. Kennard, R. Taylor, Acc. Chem. Res. 1983, 16, 146;
84. b) I. J. Bruno, J. C. Cole, P. R. Edgington, M. Kessler, C. F. Macrae, P. McCabe, J. Pearson, R. Taylor, Acta Crystallogr., Sect. B 2002, 58, 389.