Reactivity of Molybdenum and Rhenium Hydroxo-Carbonyl Complexes toward Organic Electrophiles

Chemistry - A European Journal

Volumn 10, Issue 7, 2004, Pages 1765-1777

  Cuesta, Luciano ^a   Gerbino, Darío C ^a   Hevia, Eva ^a   Morales, Dolores ^a   Navarro Clemente, M Elena ^a   Pérez, Julio ^a   Riera, Lucía ^a   Riera, Víctor ^a   Miguel, Daniel ^b   Del Río, Ignacio ^a   García Granda, Santiago ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

^b UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

Carbonyl complexes; Hydroxo complexes; Insertion; Molybdenum; Rhenium

Indexed keywords

ALDEHYDES; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RHENIUM; UREA; X RAY DIFFRACTION ANALYSIS;

ELECTROPHILES; LIGANDS;

MOLYBDENUM;

ACETALDEHYDE; BRIDGED COMPOUND; CARBON; CARBONYL DERIVATIVE; MOLYBDENUM COMPLEX; NITROGEN; ORGANIC COMPOUND; OXYGEN; PHENOL; PHENYLACETIC ACID DERIVATIVE; RHENIUM; VINYL ACETATE;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; COVALENT BOND; INFRARED SPECTROSCOPY; METALLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

MODELS, CHEMICAL; MOLECULAR STRUCTURE; MOLYBDENUM; ORGANOMETALLIC COMPOUNDS; RHENIUM;

EID: 11144356357     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305577     Document Type: Article

References (101)

1. Alkoxo complexes: a) M. H. Chisholm, J. Chem. Soc. Dalton Trans. 1996, 1781-1791;
2. b) M. H. Chisholm, Chem. Soc. Rev. 1995, 24, 79-88;
3. c) W. E. Buhro, M. H. Chisholm, Adv. Organomet. Chem. 1987, 27, 311-369;
4. d) R. R. Schrock, Polyhedron 1995, 14, 3177-3195;
5. e) C. C. Cummins, Chem. Commun. 1998, 1777-1785;
6. amido complexes: f) R. Kempe, Angew. Chem. 2000, 112, 478; Angew. Chem. Int. Ed. 2000, 39, 468-493.
7. amido complexes: f) R. Kempe, Angew. Chem. 2000, 112, 478; Angew. Chem. Int. Ed. 2000, 39, 468-493.
8. For a general (not limited to coordination compounds) monography on alkoxo and aryloxo compounds see: g) D. C. Bradley, R. C. Mehrotra, I. P. Rothwell, A. Singh, Alkoxo and Aryloxo Derivatives of Metals, Academic Press, 2001, London.
9. Reviews dealing with hydroxo, alkoxo, and amido complexes of low valent late transition metals: h) H. E. Bryndza, W. Tam, Chem. Rev. 1988, 88, 1163-1188;
10. i) R. G. Bergman, Polyhedron 1995, 14, 3227-3237.
11. F. Basolo, R. G. Pearson, Mechanisms of Inorganic Reactions, 2nd ed, Wiley, New York, 1968, pp. 177. For a recent study where this effect is found to be important in transformations of organometallic compounds see: T. C. Flood, J. K. Lim, M. A. Deming, W. Keung, Organometallics 2000, 19, 1166-1174.
12. F. Basolo, R. G. Pearson, Mechanisms of Inorganic Reactions, 2nd ed, Wiley, New York, 1968, pp. 177. For a recent study where this effect is found to be important in transformations of organometallic compounds see: T. C. Flood, J. K. Lim, M. A. Deming, W. Keung, Organometallics 2000, 19, 1166-1174.
13. H. E. Bryndza, L. K. Fong, R. A. Paciello, W. Tam, J. E. Bercaw, J. Am. Chem. Soc. 1987, 109, 1444-1456.
14. a) J. M. Mayer, Comments Inorg. Chem. 1988, 8, 125-135;
15. b) K. G. Caulton, New J. Chem. 1994, 18, 25-41.
16. For an alternative interpretation see: c) P. L. Holland, R. A. Andersen, R. G. Bergman, Comments Inorg. Chem. 1999, 21, 115-129.
17. a) F. Bottomley, L. Sutin, Adv. Organomet. Chem. 1988, 28, 339-396;
18. b) M. A. Bennett, H. Jin, S. Li, L. M. Rendina, A. C. Willis, J. Am. Chem. Soc. 1995, 117, 8335-8340;
19. c) A. Maldotti, C. Bartocci, G. Varani, A. Molinari, P. Battioni, D. Mansuy, Inorg. Chem. 1996, 35, 1126-1131;
20. d) Y. Yamamoto, X.-H. Han, J.-E Ma, Angew. Chem. 2000, 112, 2041; Angew. Chem. Int. Ed. 2000, 39, 1965-1968;
21. d) Y. Yamamoto, X.-H. Han, J.-E Ma, Angew. Chem. 2000, 112, 2041; Angew. Chem. Int. Ed. 2000, 39, 1965-1968;
22. e) A. Mori, Y. Danda, T. Fujii, K. Hirabayashi, K. Osakada, J. Am. Chem. Soc. 2001, 123, 10774-10775;
23. f) K. L. Breno, D. R. Tyler, Organometallics 2001, 20, 3864-3868;
24. g) K. L. Breno, M. D. Pluth, D. R. Tyler, Organometallics 2003, 22, 1203-1211.
25. J. R. Fulton, A. W. Holland, D. J. Fox, R. G. Bergman, Acc. Chem. Res. 2002, 35, 44-56.
26. J. W. Gilje, H. W. Roesky, Chem. Rev. 1994, 94, 895-910.
27. S. A. MacGregor, D. MacQueen, Inorg. Chem. 1999, 38, 4868-4876.
28. a) R. A. Michelin, M. Napoli, R. Ros, J. Organomet. Chem. 1979, 175, 239-255;
29. b) J-G. Ren, H. Tomita, M. Minato, T. Ito, K. Osakada, M. Yamasaki, Organometallics 1996, 15, 852-859;
30. c) A. J. Edwards, S. Elipe, M. A. Esteruelas, F. J. Lahoz, L. A. Oro, C. Valero, Organometallics 1997, 16, 3828-3836;
31. d) J. Ruiz, M. T. Martínez, F. Florenciano, V. Rodríguez, G. López, J. Pérez, P. A. Chaloner, P. B. Hitchcock, Inorg. Chem. 2003, 42, 3650-3661;
32. e) C. Bergquist, T. Fillebeen, M. M. Morlok, G. Parkin, J. Am. Chem. Soc. 2003, 125, 6189-6199.
33. K. A. Woerpel, R. G. Bergman, J. Am. Chem. Soc. 1993, 115, 7888-7889.
34. a) M. D. Fryzuk, C. D. Montgomery, Coord. Chem. Rev. 1989, 95, 1-40;
35. b) L. M. Green, D. W. Meek, Organometallics 1989, 8, 659-666;
36. c) A. W. Kaplan, R. G. Bergman, Organometallics 1998, 17, 5072-5085;
37. d) J. Kovács, T. D. Todd, J. H. Reibenspies, F. Joó, D. J. Darensbourg, Organometallics 2000, 19, 3963-3969.
38. a) E. Hevia, J. Pérez, L. Riera, V. Riera, D. Miguel, Organometallics 2002, 21, 1750-1752;
39. b) E. Hevia, J. Pérez, L. Riera, V. Riera, I. del Río, S. García-Granda, D. Miguel, Chem. Eur. J. 2002, 8, 4510-4521.
40. 2 has been published: D. C. Gerbino, E. Hevia, D. Morales, M. E. N. Clemente, J. Pérez, L. Riera, V. Riera, D. Miguel, Chem. Commun. 2003, 328-329. Those results are substantially different than the ones included here, and will not be republished in the present paper.
41. D. Morales, M. E. N. Clemente, J. Pérez, L. Riera, V. Riera, D. Miguel, Organometallics 2002, 21, 4934-4938.
42. The hydroxo complexes 2a and 2b were previously synthesized by a similar method, see ref. [16]. We mentioned their preparation here to show that the presence or absence of water has the same effect as for the aforementioned molybdenum complexes. Experimental details are given as Supporting Information.
43. a) D. H. Gibson, X. Yin, J. Am. Chem. Soc. 1998, 120, 11200-11201;
44. b) D. H. Gibson, X. Yin, H. Hen, M. S. Mashuta, Organometallics 2003, 22, 337-346.
45. 6 salt, and its X-ray characterization were reported when this manuscript was in preparation: P. J. Heard, P. Sroisuwan, D. A. Tocher, Polyhedron 2003, 22, 1321-1327.
46. 2(phenanthroline)] toward KOH, see reference [14].
47. In this reaction, half of the hydroxo complex is transformed into the cationic aquo complex, whose labile water ligand is then displaced by the hydroxo ligand of the non-reacted hydroxo complex to afford the OH-bridged product.
48. Tables of distances and angles of all the compounds whose structures were determined by X-ray diffraction are included as Supporting Information.
49. 3] fragments see reference [22] and reference [23], respectively.
50. a) K. R. Breakell, S. J. Rettig, A. Storr, J. Trotter, Can. J. Chem. 1979, 57, 139-146;
51. b) S.-F. Lush, S.-H. Wang, G.-H. Lee, S.-M. Peng, S.-L. Wang, R.-S. Liu, Organometallics 1990, 9, 1862-1871;
52. c) C. Borgmann, C. Limberg, E. Kaifer, H. Pritzkow, L. Zsolnai, J. Organomet. Chem. 1999, 580, 214-224;
53. d) C. Borgmann, C. Limberg, S. Cunskis, P. Kircher, Eur. J. Inorg. Chem. 2001, 349-352.
54. W. Wang, Y. K. Yan, T. S. A. Hor, J. J. Vittal, J. R. Wheaton, I. H. Hall, Polyhedron 2002, 21, 1991-1999.
55. a) C. Balzarek, T. J. R. Weakley, L. Y. Kuo, D. R. Tyler, Organometallics 2000, 19, 2927-2931;
56. b) R. W. McGaff, N. C. Dopke, R. K. Hayashi, D. R. Powell, P. M. Treichel, Polyhedron 2000, 19, 1245-1254.
57. E. Hevia, J. Pérez, V. Riera, D. Miguel, S. Kassel, A. Rheingold, Inorg. Chem. 2002, 41, 4673-4679.
58. W. R. Scheidt, B. Cheng, M. K. Safo, F. Cukiernik, J-C. Marchon, P. G. Debrunner, J. Am. Chem. Soc. 1992, 114, 4420-4421.
59. For reactions of organometallic complexes with isocyanates see: P. Braunstein, D. Nobel, Chem. Rev. 1989, 89, 1927-1945.
60. K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination compounds. Part B: Applications in Coordination, Organometallic and Bioinorganic Chemistry, 5th ed. Wiley, 1997, New York.
61. A. G. Orpen, L. Brammer, F. H. Allen, O. Kennard, D. G. Watson, R. Taylor, J. Chem. Soc. Dalton Trans. 1989, 1-83.
62. 1(O): a) Ref. [9d] and [16b];
63. b) R. A. Michelin, G. Strukul, N. Bresciani-Pahor, E. Zangrando, L. Randaccio, Inorg. Chim. Acta 1984, 84, 229-232;
64. c) M. K. Reinking, J. Ni, P. E. Fanwick, C. P. Kubiak, J. Am. Chem. Soc. 1989, 111, 6459-6461;
65. d) D. A. Brown, D. M. Kimari, A. M. Duzs-Moore, T. A. Budzichowski, D. M. Ho, S. K. Mandal, J. Organomet. Chem. 2002, 658, 88-93.
66. Other coordination modes: e) J. Breimair, C. Robl, W. Beck, J. Organomet. Chem. 1991, 411, 395-404;
67. f) M.-C. Suen, G.-W Tseng, J.-D. Chen, T.-C. Keng, J.-C. Wang, Chem. Commun. 1999, 1185-1186;
68. g) F. A. Cotton, C. Lin, C. A. Murillo, J. Am. Chem. Soc. 2001, 123, 2670-2671.
69. Examples of Mo(CO) fragments that contain carbonate bridges: h) E. Carmona, F. González, M. L. Poveda, J. M. Marin, J. L. Atwood, R. D. Rogers, J. Am. Chem. Soc. 1983, 105, 3365-3366;
70. i) R. Alvarez, E. Carmona, A. Galindo, E. Gutiérrez, E. Marin, A. Monge, M. L. Poveda, C. Ruíz, J. M. Savariault, Organometallics 1989, 8, 2430-2439;
71. j) R. Alvarez, J. L. Atwood, E. Carmona, P. Pérez, M. L. Poveda, R. D. Rogers, Inorg. Chem. 1991, 30, 1493-1499.
72. D. J. Darensbourg, M. L. Meckfessel Jones, J. H. Reibenspies, Inorg. Chem. 1993, 32, 4675-4676.
73. E. Hevia, J. Pérez, V. Riera, D. Miguel, Chem. Commun. 2002, 1814-1815.
74. E. Hevia, J. Pérez, V. Riera, D. Miguel, Organometallics 2003, 22, 257-263.
75. J. March, Advanced Organic Chemistry. Reactions, Mechanisms and Structure, 4th ed, Wiley, 1992, New York.
76. Hydrolysis of metallacarbonate ester complexes to give carbonate complexes has previously been observed: a) T. Yoshida, T. Okano, Y. Ueda, S. Otsuka, J. Am. Chem. Soc. 1981, 103, 3411-3422;
77. b) D. J. Darensbourg, K. M. Sanchez, J. H. Reibenspies, A. L. Rheingold, J. Am. Chem. Soc. 1989, 111, 7094-7103;
78. c) R. D. Simpson, R. G. Bergman, Organometallics 1992, 11, 4306-4315.
79. R. Alsfasser, S. Trofimenko, A. Looney, G. Parkin, H. Vahrenkamp, Inorg. Chem. 1991, 30, 4098-4100.
80. D. H. Gibson, B. A. Sleaad, X. Yin, A. Vij, Organometallics 1998, 17, 2689-2691.
81. M-OH bonds have been found to be stronger than M-OR bonds in related compounds, see reference [3].
82. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc. Perkin Trans. 2 1987, 1-19.
83. D. Morales, J. Pérez, L. Riera, V. Riera, D. Miguel, M. E. G. Mosquera, S. García-Granda, Chem. Eur. J. 2003, 9, 4132-4143.
84. II complexes: a) J. Pérez, V. Riera, A. Rodríguez, S. García-Granda, Angew. Chem. 2002, 114, 1485; Angew. Chem. Int. Ed. 2002, 41, 1427-1429;
85. II complexes: a) J. Pérez, V. Riera, A. Rodríguez, S. García-Granda, Angew. Chem. 2002, 114, 1485; Angew. Chem. Int. Ed. 2002, 41, 1427-1429;
86. b) J. Pérez, V. Riera, A. Rodríguez, R. López, T. L. Sordo, S. García-Granda, E. García-Rodríguez, A. Galindo, Organometallics 2003, 22, 1540-1545.
87. Examples of pseudo-octahedral allyl monocarbonyl complexes: c) K.-H. Yih, G.-H. Lee, S. L. Huang, Y. Wang, Inorg. Chim. Acta 2003, 348, 271-278;
88. d) K.-H. Yih, G.-H. Lee, S.-L. Huang, Y. Wang, Organometallics 2002, 21, 5767-5774.
89. However, formation of metallacycles that involve a CO group and a complex that contains a basic ligand (thiolato or phosphido) as a result of its reaction with DMAD has previously been observed: M. T. Ashby, J. H. Enemark, Organometallics 1987, 6, 1318-1323.
90. a) J. Pérez, L. Riera, V. Riera, S. García-Granda, E. García-Rodríguez, J. Am. Chem. Soc. 2001, 123, 7469-7470;
91. b) J. Pérez, L. Riera, V. Riera, S. García-Granda, E. García-Rodríguez, D. Miguel, Organometallics 2002, 21, 1622-1626;
92. c) D. Morales, J. Pérez, L. Riera, V. Riera, D. Miguel, Inorg. Chem. 2002, 41, 4111-4113.
93. J. Guerrero, O. E. Pino, E. Wolcan, M. R. Feliz, G. Ferraudi, S. A. Moya, Organometallics 2001, 20, 2842-2853.
94. SAINT+. SAX area detector integration program. Version 6.02. Bruker AXS, Inc. Madison, WI, 1999.
95. Sheldrick, G. M. SHELXTL, An integrated system for solving, refining, and displaying crystal structures from diffraction data. Version 5.1. Bruker AXS, Inc. Madison, WI, 1998.
96. Sheldrick, G. M. SADABS. Empirical Absorption Correction Program. University of Göttingen: Göttingen, Germany, 1997.
97. P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, S. García-Granda, R. O. Gould, J. M. M. Smits, C. Smykalla, (1992). The DIRDIF program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands.
98. G. M. Sheldrick, SHELXL-97, University of Göttingen, A computer program for refinement of crystal structures, 1997.
99. S. Parking, B. Moezzi, H. Hope, J. Appl. Crystallogr. 1995, 28, 53-56.
100. M. Nardelli, Comput. Chem. 1983, 7, 95-98.
101. A. L. Spek, PLATON, a multipurpose crystallo-graphic tool, Utrecht University, Utrecht, The Netherlands, 2001.