Reactivity of indenyl-ruthenium(II) vinylidene complexes: Selective synthesis of alkenyl-phosphonio derivatives via nucleophilic addition of triphenylphosphine on their η2-alkyne tautomers. Theoretical study of the η1-vinylidene-η2-alkyne tautomerization

Organometallics

Volumn 20, Issue 24, 2001, Pages 5177-5188

  Cadierno, Victorio ^a   Gamasa, M Pilar ^a   Gimeno, José ^a   González Bernardo, Covadonga ^a   Pérez Carreño, Enrique ^a   García Granda, Santiago ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL-PHOSPHONIO DERIVATIVES; ALKYNE; DICHLOROMETHANE; INDENYL-RUTHENIUM VINYLIDENE COMPLEXES; NUCLEOPHILIC ADDITION; TAUTOMERIZATION; TRIPHENYLPHOSPHINE;

ADDITION REACTIONS; CRYSTAL STRUCTURE; LOW TEMPERATURE PROPERTIES; METHANOL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL); TEMPERATURE; X RAY DIFFRACTION ANALYSIS;

ORGANOMETALLICS;

EID: 0035956466     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om010308e     Document Type: Article

References (118)

1. (a) Antonova, A. B.; Ioganson, A. A. Russ. Chem. Rev. (Engl. Transl.) 1989, 58, 693.
2. (b) Bruce, M. I. Chem. Rev. 1991, 91, 197.
3. (c) Werner, H. Nachr. Chem. Technol. Lab. 1992, 40, 435.
4. (d) Werner, H. J. Organomet. Chem. 1994, 475, 45.
5. (e) Brueneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311.
6. (f) Puerta, M. C.; Valerga, P. Coord. Chem. Rev. 1999, 193-195, 977.
7. Ruthenium(II) vinylidene complexes have been shown to be excellent promoters for selective C-C coupling reactions. (a) Slugovc, C.; Mereiter, K.; Schmid, R.; Kirchner, K. J. Am. Chem. Soc. 1998, 120, 6175.
8. (b) Jia, G.; Lau, C. P. J. Organomet. Chem. 1998, 565, 37, and references therein.
9. (c) Yi, C. S.; Liu, N. Organometallics 1998, 17, 3158.
10. (d) Huang, D.; Oliván, M.; Huffman, J. C.; Eisenstein, O.; Caulton, K. G. Organometallics 1998, 17, 4700.
11. (e) Yam, V. W. W.; Chu, B. W. K.; Cheung, K. K. Chem. Commun. 1998, 2261.
12. (f) Slugovc, C.; Mereiter, K.; Schmid, R.; Kirchner, K. Eur. J. Inorg. Chem. 1999, 1141.
13. (g) Jiménez Tenorio, M. A.; Jiménez Tenorio, M.; Puerta, M. C.; Valerga, P. Organometallics 2000, 19, 1333.
14. (h) Bruce, M. I.; Hall, B. C.; Skelton, B. W.; White, A. H.; Zaitseva, N. N. J. Chem. Soc., Dalton Trans. 2000, 2279.
15. (i) Lin, Y. C. J. Organomet. Chem. 2001, 617-618, 141, and references therein.
16. (j) Pavlik, S.; Gemel, C.; Slugovc, C.; Mereiter,K.; Schmid, R.; Kirchner, K. J. Organomet. Chem. 2001, 617-618, 301, and references therein.
17. They are also active catalysts for the ring-opening metathesis polymerization (ROMP) of olefines: (k) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.
18. (l) Katayama, H.; Ozawa, F. Chem. Lett. 1998, 67.
19. (m) Katayama, H.; Yoshida, T.; Ozawa, F. J. Organomet. Chem. 1998, 562, 203.
20. (n) del Rio, I.; van Koten, G. Tetrahedron Lett. 1999, 40, 1401.
21. (o) Katayama, H.; Urushima, H.; Ozawa, F. J. Organomet. Chem. 2000, 606, 16.
22. (p) Saoud, M.; Romerosa, A.; Peruzzini, M. Organometallics 2000, 19, 4005.
23. β atom of the alkynyl group to afford the final vinylidene tautomer [Ru{=C=C(H)R}]:
24. (b) de los Rios, I.; Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P. J. Am. Chem. Soc. 1997, 119, 6529.
25. (c) Bustelo, E.; Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P. Organometallics 1999, 18, 4563.
26. 8 (Co(I), Rh(I), Ir(I)) metal complexes have been theoretically [(d) Wakatsuki, Y.; Koga, N.; Werner, H.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 360.
27. (e) Pérez-Carreño, E.; Paoli, P.; Ienco, A.; Mealli, C. Eur. J. Inorg. Chem. 1999, 1315.] and experimentally proved to occur also through this oxidative mechanism. See for example, the following. Co(I):
28. (f) Bianchini, C.; Peruzzini, M.; Vacca, A.; Zanobini, F. Organometallics 1991, 10, 3697.
29. Rh(I): (g) Windmüller, B.; Wolf, J.; Werner, H. J. Organomet. Chem. 1995, 502, 147.
30. (h) Werner, H.; Gevert, O.; Steinert, P.; Wolf, J. Organometallics 1995, 14, 1786.
31. (i) Wiedemann, R.; Fleischer, R.; Stalke, D.; Werner, H. Organometallics 1997, 16, 866.
32. (j) Kovacik, I.; Laubender, M.; Werner, H. Organometallics 1997, 16, 5607, and references therein.
33. Ir(I): (k) Lass, R. W.; Steinert, P.; Wolf, J.; Werner, H. Chem. Eur. J. 1996, 2, 19.
34. (l) Werner, H.; Lass, R. W.; Gevert, O.; Wolf, J. Organometallics 1997, 16, 4077, and references therein.
35. (a) Bullock, R. M. J. Chem. Soc., Chem. Commun. 1989, 165.
36. (b) Lomprey, J.R.; Selegue, J. P. J. Am. Chem. Soc. 1992, 114, 5518.
37. + is stable only under an acetylene atmosphere indicating a reversible process: (a) Martín, M.; Gevert, O.; Werner, H. J. Chem. Soc., Dalton Trans. 1996, 2275.
38. 2-alkyne complex. See ref 5a and: (b) Bianchini, C.; Purches, G.; Zanobini, F.; Peruzzini, M. Inorg. Chim. Acta 1998, 272, 1.
39. (c) Gemel, C.; Huffman, J. C.; Caulton, K. G.; Mauthner, K.; Kirchner, K. J. Organomet. Chem. 2000, 593-594, 342.
40. 3)], respectively. See ref 4a and: (d) Albertin, G.; Antoniutti, S.; Bordignon, E.; Cazzaro, F.; Ianelli, S.; Pellizi, G. Organometallics 1995, 14, 4114.
41. (e) Slugovc, C.; Sapunov, V. N.; Wiede, P.; Mereiter, K.; Schmid, R.; Kirchner, K. J. Chem. Soc., Dalton Trans. 1997, 4209.
42. 3)] with phosphites has been also reported: (f) Bruce, M. I.; Hall, B. C.; Zaitseva, N. N.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1996, 522, 307.
43. Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Pérez-Carreño, E.; García-Granda, S. Organometallics 1999, 18, 2821.
44. (a) Cadierno, V.; Conejero, S.; Gamasa, M. P.; Gimeno, J. J. Chem. Soc., Dalton Trans. 2000, 451.
45. (b) Cadierno, V.; Gamasa, M. P.; Gimeno, J. J. Organomet. Chem. 2001, 621, 39.
46. (c) Cadierno, V.; Conejero, S.; Gamasa, M. P.; Gimeno, J.; Pérez-Carreño, E.; García-Granada, S. Organometallics 2001, 20, 3175.
47. Gamasa, M. P.; Gimeno, J.; González-Bernardo, C.; Borge, J.; García-Granda, S. Organometallics 1997, 16, 2483.
48. (a) Cadierno, V.; Díez, J. Gamasa, M. P.; Gimeno, J.; Lastra, E. Coord. Chem. Rev. 1999, 193-195, 147.
49. (b) Gamasa, M. P.; Gimeno, J.; González-Bernardo, C. Manuscript in preparation.
50. 2-HC≡CPh) protons are in accordance with data reported in the literature. See refs 3b,c, 4 and: Nombel, P.; Lugan, N.; Mathieu, R. J. Organomet. Chem. 1995, 503, C22.
51. 3) (Figure 5).
52. (a) Gamasa, M. P.; Gimeno, J.; Martín-Vaca, B. M.; Borge, J.; García-Granda, S.; Pérez-Carreño, E. Organometallics 1994, 13, 4045.
53. (b) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Borge, J.; García-Granda, S. J. Chem. Soc., Chem. Commun. 1994, 2495.
54. (c) Gamasa, M. P.; Gimeno, J.; Godefroy, I.; Lastra, E.; Martín-Vaca, B.M.; García-Granda, S.; Gutierrez-Rodriguez, A. J. Chem. Soc., Dalton Trans. 1995, 1901.
55. (d) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; González-Cueva, M.; Lastra, E.; Borge, J.; García-Granda, S. Organometallics 1996, 15, 2137.
56. (e) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Borge, J.; García-Granda, S. Organometallics 1997, 16, 3178.
57. (f) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; López-González, M. C.; Borge, J.; García-Granda, S. Organometallics 1997, 16, 4453.
58. (g) Crochet, P.; Demerseman, B.; Vallejo, M. I.; Gamasa, M. P.; Gimeno, J.; Borge, J.; García-Granda, S. Organometallics 1997, 16, 5406.
59. (h) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Moretó, J. M.; Ricart, S.; Roig, A.; Molins, E. Organometallics 1998, 17, 697.
60. (i) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Pérez-Carreño, E.; Ienco, A. Organometallics 1998, 17, 5216.
61. (j) Cadierno, V.; Conejero, S.; Gamasa, M. P.; Gimeno, J.; Asselberghs, I.; Houbrechts, S.; Clays, K.; Persoons, A.; Borge, J.; García-Granda, S. Organometallics 1999, 18, 582.
62. (k) Cadierno, V.; Gamasa, M. P.; Gimeno, J. J. Chem. Soc., Dalton Trans. 1999, 1857.
63. (l) Cadierno, V. Gamasa, M. P.; Gimeno, J.; Lastra, E. J. Chem. Soc., Dalton Trans. 1999, 3235.
64. (m) Sato, M.; Iawa, A.; Watanabe, M. Organometallics 1999, 18, 3208.
65. Literature precedents for selective phosphine attack on coordinated alkynes to generated (E)-alkenyl-phosphonio complexes include: (a) J. Organomet. Chem. 1982, 238, 223.
66. (b) Hoffman, D. M.; Huffman, J. C.; Lappas, D.; Wierda, D. A. Organometallics 1993, 12, 4312.
67. (c) Williams, D. S.; Schofield, M. H.; Schrock, R. R. Organometallics 1993, 12, 4560.
68. (d) Jung, J. H.; Hoffman, D. M.; Lee, T. R. J. Organomet. Chem. 2000, 599, 112.
69. (e) Hansen, H. D.; Nelson, J. H. Organometallics 2000, 19, 4740.
70. (a) Bassetti, M.; Casellato, P.; Gamasa, M. P.; Gimeno, J.; González-Bernardo, C.; Martín-Vaca, B. Organometallics 1997, 16, 5470.
71. (b) Gamasa, M. P.; Gimeno, J.; Martín-Vaca, B. M. Organometallics 1998, 17, 3707.
72. (c) Cadierno, V.; Gamasa, M. P.; Gimeno, J.; Martín-Vaca, B. M. J. Organomet. Chem. 2001, 617-618, 261.
73. Kostic, N. M.; Fenske, R. J. Organometallics 1982, 1, 974.
74. Bruce, M. I.; Catlow, A.; Humphrey, M. G.; Koutsantonis, G. A.; Snow, M. R.; Tiekink, E. R. T. J. Organomet. Chem. 1988, 338, 59.
75. Torres, M. R.: Santos, A.; Perales, A; Ros, J. J. Organomet. Chem. 1998, 353, 321.
76. Romero, A.; Santos, A. Vegas, A. Organometallics 1988, 7, 1988.
77. López, J.; Santos, A.; Romero, A; Echevarren, A. M. J. Organomet. Chem. 1993, 443, 221.
78. Bohanna, C.; Esteruelas, M.; Lahoz, F. J.; Oñate, E.; Oro, L. A. Organometallics 1995, 14, 4685.
79. (a) Silvestre, J.; Hoffmann, R. Helv. Chim. Acta 1985, 68, 1461.
80. (b) Stegmann, R.; Frenking, G. Organometallics 1998, 17, 2089.
81. (c) García-Yebra, C.; López-Mardomingo, C.; Fajardo, M.; Antiñolo, A.; Otero, A.; Rodríguez, A.; Vallat, A.; Lucas, D.; Mugnier, Y.; Carbó, J. J.; Lledós, A.; Bo, C. Organometallics 2000, 19, 1749.
82. Kitaura, K.; Sakaki, S.; Morokuma, K. Inorg. Chem. 1981, 20, 2292.
83. Pérez-Carreño, E. Doctoral Thesis, University of Oviedo, 1996.
84. Oliván, M.; Clot, E.; Eisenstein, O.; Caulton, K. G. Organometallics 1998, 17, 3091.
85. 5 complexes
86. (b) Abd-Alzaher, M. M.; Fischer, H. J. Organomet. Chem. 1999, 588, 235.
87. 5)(CO)(NO)] has been also described:
88. 2OEt) are rather labile the dissociation of which gives the free alkyne:
89. (e) Albertin, G.; Antoniutti, S.; Bordignon, E.; Bresolin, D. J. Organomet. Chem. 2000, 609, 10.
90. (f) Albertin, G.; Antonitti, S.; Bordignon, E.; Pegoraro, M. J. Chem. Soc., Dalton Trans. 2000, 3575.
91. Reger, D. L. Acc. Chem. Res. 1988, 21, 229, and references therein.
92. 3): (a) Kolobova, N. Y.; Stripkin, V. V.; Alexandrof, G. G.: Struchkov, Y. T. Kolobova, N. Y.; Stripkin, V. V.; Alexandrof, G. G.: Struchkov, Y. T. J. Organomet. Chem. 1979, 169, 293.
93. (b) Boland-Lussier, B. E.; Churchill, M. R.; Hughes, R. P.; Rheingold, A. L. Organometallics 1982, 1, 628.
94. +, respectively: (c) Senn, D. R.; Wong, A.; Patton, A. T.; Marsi, M.; Strouse, C. E.; Gladysz, J. A. J. Am. Chem. Soc. 1988, 110, 6096.
95. Kolobova, N. E.; Skripkin, V. V.; Rozantseva, T. V. Izv. Akad. Nauk SSSR, Ser. Khim. 1979, 2393.
96. 2, R = Ph): (e) Antonova, A. B.; Kolobova, N. E.; Petrovsky, P. V.; Lokshin, B. V.; Obezyuk, N. S. J. Organomet. Chem. 1977, 137, 55.
97. (f) Nesmeyanov, A. N.; Kolobova, N. E.; Antonova, A. B.; Obezyuk N. S.; Anisimov, K. N. Izv. Akad. Nauk SSSR, Ser. Khim. 1976, 948.
98. (g) Antonova, A. B.; Gubin, S. P.; Kovalenko, S. V. Izv. Akad. Nauk SSSR, Ser. Khim. 1982, 953.
99. α carbon of the vinylidene fragment: (h) Ipaktschi, J.; Klotzbach, T.; Dulmer, A. Organometallics 2000, 19, 5281.
100. α is also know. See for example: (i) Bianchini, C.; Meli, A.; Peruzzini, M.; Zanobini, F.; Zanello, P. Organometallics 1990, 9, 241.
101. For reviews on reactivity of allenylidene conplexes see: (a) Werner, H. Chem. Commun. 1997, 903.
102. (b) Touchard, D.; Dixneuf, P. H. Coord. Chem. Rev. 1998, 178-180, 409.
103. (c) Bruce, M. I. Chem. Rev. 1998, 98, 2797.
104. (d) Cadierno, V.; Gamasa, M. P.; Gimeno, J. Eur. J. Inorg. Chem. 2001, 571.
105. Grant, D. F.; Gabe, E. J. J. Appl. Crystallogr. 1978, 11, 114.
106. Lehman, M. S.; Larsen, F. K. Acta Crystallogr., Sect. A 1974, 30, 580.
107. Beurkens, P. T.; Admiraal, G.; Beurkens, G.; Bosman, W. P.; García-Granda, S.; Gould, R. O.;Smits, J. M. M.; Smykalla, C. The DIRDIF Program System; Technical Report; Crystallographic Laboratory, University of Nijmegen, The Netherlands, 1992.
108. Sheldrick, G. M. SHELXL93. In Crystallographic Computing 6; Flack, P., Parkanyi, P., Simon, K., Eds.; IUCr/Oxford University Press: Oxford, U.K., 1993.
109. International Tables for X-ray Crystallography; Kynoch Press: Birminghan, U.K., 1974; Vol. IV.
110. Nardelli, M. Comput. Chem. 1983, 7, 95.
111. Spek, A. L. The EUCLID Package. In Computational Crystallography; Sayre, D., Ed.; Clarendon Press: Oxford, U.K., 1982; p 528.
112. Spek, A. L. Acta Crystallogr., Sect. A 1990, 46, C34.
113. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuk, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T. A.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98 (Revision A.7); Gaussian Inc.: Pittsburgh, PA, 1998.
114. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
115. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
116. Höllwarth, A.; Böhme, M.; Dapprich, S.; Ehlers, A. W.; Gobbi, A.; Jonas, V.; Köhler, K.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 237.
117. Hariharan, P. C.; Pople, J. Theor. Chim. Acta 1973, 28, 213.
118. Hehre, W. J.; Stewart, R. F.; Pople, J. A. J. Chem. Phys. 1969, 51, 2657.