Recent developments in the reactivity of allenylidene and cumulenylidene complexes

European Journal of Inorganic Chemistry

Volumn , Issue 3, 2001, Pages 571-591

  Cadierno, Victorio ^a   Gamasa, M Pilar ^a   Gimeno, José ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Alkynyl complexes; Allenylidene complexes; Carbene complexes; Cumulenylidene complexes; Vinylidene complexes

Indexed keywords

CATALYSIS; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

ALKYNYL COMPLEXES; ALLENYLIDENE COMPLEXES; ALLENYLIDENES; CARBENE CHEMISTRY; CARBENE COMPLEXES; CATALYTIC REACTIONS; CUMULENYLIDENE COMPLEX; METAL CARBENES; STOICHIOMETRIC REACTION; VINYLIDENE COMPLEXES;

TRANSITION METALS;

ALCOHOL DERIVATIVE; ALLENYLIDENE; AMINE; BUTATRIENYLIDENE COMPLEX; CARBENOID; CUMULENYLIDENE; PENTATETRAENYLIDENE COMPLEX; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYLIDENE COMPLEX;

CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; INFRARED SPECTROSCOPY; ISOMERISM; MOSSBAUER SPECTROSCOPY; REACTION ANALYSIS; SHORT SURVEY; STEREOCHEMISTRY; STOICHIOMETRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 0035112467     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0682(200103)2001:3<571::AID-EJIC571>3.0.CO;2-2     Document Type: Short Survey

References (128)

1. For recent reviews see: [1a] W. D. Wulff, in: Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon Press, Oxford, 1991, vol. 5, p. 1065-1113. -
2. [1b] M. J. Winter, in: Comprehensive Organometallic Chemistry II (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon Press, Oxford, 1995, vol. 5, p. 155-214. -
3. [1c] M. P. Doyle, in: Comprehensive Organometallic Chemistry II (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon Press, Oxford, 1995, vol. 5, p. 387-468. -
4. [1d] W. D. Wulff, in: Comprehensive Organometallic Chemistry II (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon Press, Oxford, 1995, vol. 12, p. 469-547. -
5. [1e] L. S. Hegedus, in: Comprehensive Organometallic Chemistry II (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon Press, Oxford, 1995, vol. 12, p. 549-576. -
6. [1f] D. F. Harvey, D. M. Sigano, Chem. Rev. 1996, 96, 271-288. -
7. [1g]. Zaragoza Dörwald, in: Metal Carbenes in Organic Synthesis, Wiley-VCH, Weinheim, 1999.
8. For recent reviews see: [2a] W. Beck, B. Niemer, M. Wieser, Angew. Chem. Int. Ed. Engl. 1993, 32, 923-949. -
9. [2b] H. Lang, Angew. Chem. Int. Ed. Engl. 1994, 33, 547-550. -
10. [2c] U. H. F. Bunz, Angew. Chem. Int. Ed. Engl. 1996, 35, 969-973. -
11. [2d] F. Paul, C. Lapinte, Coord. Chem. Rev. 1998, 178-180, 431-509. -
12. [2e] See also: R. Dembinski, T. Bartik, B. Bartik, M. Jaeger, J. A. Gladysz, J. Am. Chem. Soc. 2000, 122, 810-822 and references cited therein.
13. For recent reviews see: [3a] R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452. -
14. [3b] M. Schuster, S. Blechert, Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2056. -
15. [3c] R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450.
16. [4a] M. I. Bruce, Chem Rev. 1991 91, 197-257. -
17. [4b] M. I. Bruce, Chem. Rev. 1998, 98, 2797-2858. -
18. [4c] H. Werner, Chem. Commun. 1997, 903-910. -
19. [4d] H. Le Bozec, P. H. Dixneuf, Russ. Chem. Bull. 1995, 44, 801-812. -
20. [4e] D. Touchard, P. H. Dixneuf, Coord. Chem. Rev. 1998, 178-180, 409-429. -
21. [4f] M. I. Bruce, Coord. Chem. Rev. 1997, 166, 91-119. -
22. [4g] S. Doherty, J. F. Corrigan, A. J. Carty, E. Sappa, Adv. Organomet. Chem. 1995, 37, 39-130. -
23. [4h] H. El Amouri, M. Gruselle, Chem. Rev. 1996, 96, 1077-1103. -
24. [4i] G. Jia, C. P. Lau, J. Organomet. Chem. 1998, 565, 37-48.
25. [5a] E. O. Fischer, H. J. Kalder, A. Frank, F. H. Kohler, G. Huttner, Angew. Chem. Int. Ed. Engl. 1976, 15, 623-624. -
26. [5b] H. Berke, Angew. Chem. Int. Ed. Engl. 1976, 15, 624.
27. [6a] J. P. Selegue, Organometallics 1982, 1, 217-218. -
28. [6b] A. F. Hill, in: Comprehensive Organometallic Chemistry II (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon Press, Oxford, 1995, vol. 7, p. 348-356.
29. 3)], is known: P. Binger, P. Müller, R. Wenz, R. Mynott, Angew. Chem. Int. Ed. Engl. 1990, 29, 1037-1038.
30. H. J. Schanz, L. Jafarpour, E. D. Stevens, S. P. Nolan, Organometallics 1999, 18, 5187-5190.
31. See for example: [9a] J. Huang, E. D. Stevens, S. P. Nolan, J. L. Petersen, J. Am. Chem. Soc. 1999, 121, 2647-2678. -
32. [9b] J. Huang, H.-J. Schanz, E. D. Stevens, S. P. Nolan, Organometallics 1999, 18, 2370-2375.
33. D. Touchard, P. Haquette, A. Daridor, A. Romero, P. H. Dixneuf, Organometallics 1998, 17, 3844-3852.
34. E. Bustelo, M. Jiménez Tenorio, M. C. Puerta, P. Valerga, Organometallics 1999, 18, 4563-4573.
35. M. I. Bruce, P. Hinterding, P. J. Low, B. W. Skelton, A. H. White, J. Chem. Soc., Dalton Trans. 1998, 467-473.
36. L. Jafarpour, J. Huang, E. D. Stevens, S. P. Nolan, Organometallics 1999, 18, 3760-3763.
37. K. Urtel, A. Frick, G. Huttner, L. Zsolnai, P. Kircher, P. Rutsch, E. Kaifer, A. Jacobi, Eur. J. Inog. Chem. 2000, 33-50.
38. B. Buriez, I. D. Burns, A. F. Hill, A. J. P. White, D. J. Williams, J. D. E. T. Wilton-Ely, Organometallics 1999, 18, 1504-1516.
39. V. Cadierno, M. P. Gamasa, J. Gimeno, L. Iglesias, S. García-Granda, Inorg. Chem. 1999, 38, 2874-2879.
40. B. Windmüller, O. Nürnberg, J. Wolf, H. Werner, Eur. J. Inorg. Chem. 1999, 613-619.
41. C. Bianchini, M. Peruzzini, F. Zanobini, C. Lopez, I. de los Rios, A. Romerosa, Chem. Commun. 1999, 443-444.
42. H. Werner, C. Grünwald, P. Steinert, O. Gevert, J. Wolf, J. Organomet. Chem. 1998, 565, 231-241.
43. K. Ilg, H. Werner, Organometallics 1999, 18, 5426-5428.
44. H. P. Xia, W. S. Ng, J. S. Ye, X.-Y. Li, W. T. Wong, Z. Lin, C. Yang, G. Jia, Organometallics 1999, 18, 4552-4557.
45. M. Sato, A. Iwai, M. Watanabe, Organometallics 1999, 18, 3208-3219.
46. M. Tamm, A. Grzegorzewski, I. Brüdcam, H. Hartl, J. Chem. Soc., Dalton Trans. 1998, 3523-3528.
47. M. Laubender, H. Werner, Chem. Eur J. 1999, 5, 2937-2946.
48. S. B. Falloon, S. Szafert, A. M. Arif, J. A. Gladysz, Chem. Eur J. 1998, 4, 1033-1042.
49. C. J. Adams, M. I. Bruce, B. W. Skelton, A. H. White, J. Organomet. Chem. 1999, 584, 254-264.
50. M. I. Bruce, B. W. Skelton, A. H. White, N. N. Zaitseva, J. Chem. Soc., Dalton Trans. 2000, 881-890.
51. M.-C. Chung, A. Sakurai, M. Akita, Y. Moro-oka, Organometallics 1999, 18, 4684-4691.
52. [29a] S. Kheradmandan, K. Heinze, H. W. Schmalle, H. Berke, Angew. Chem. Int. Ed. 1999, 38, 2270-2273. -
53. [29b] M. Guillemot, L. Toupet, C. Lapinte, Organometallics 1998, 17, 1928-1930.
54. T. Bartik, W. Weng, J. A. Ramsden, S. Szafert, S. B. Falloon, A. M. Arif, J. A. Gladysz, J. Am. Chem. Soc. 1998, 120, 11071-11081.
55. V. Guillaume, P. Thominot, F. Coat, A. Mari, C. Lapinte, J. Organomet. Chem. 1998, 565, 75-80.
56. F. Coat, M. Guillemot, F. Paul, C. Lapinte, J. Organomet. Chem. 1999, 578, 76-84.
57. B. E. R. Schilling, R. Hoffmann, D. L. Lichtenberger, J. Am. Chem. Soc. 1979, 101, 585-591.
58. [34a] H. Berke, G. Huttner, J. von Seyerl, Z. Naturforsch. 1981, 36b, 1277-1288. -
59. [34b] N. E. Kolobova, L. L. Ivanov, O. S. Zhvanko, O. M. Khitrova, A. S. Batsanov, Y.-T. Struchkov, J. Organomet. Chem. 1984, 262, 39-47. -
60. [34c] N. E. Kolobova, L. L. Ivanov, O. S. Zhvanko, O. M. Khitrova, A. S. Batsanov, Y.-T. Struchkov, J. Organomet. Chem. 1984, 265, 271-281.
61. E. Pérez-Carreño, Ph. D. Thesis, University of Oviedo, 1996.
62. [36a] J. Díez M. P. Gamasa, J. Gimeno, C. Gónzalez-Bernardo, E. Pérez-Carreño, unpublished results. -
63. [36b] C. Gónzalez-Bernardo, M. P. Gamasa, J. Gimeno, L. Iglesias, unpublished results.
64. M. A. Esteruelas, A. V. Gómez, A. M. López, J. Modrego, E. Oñate, Organometallics 1997, 16, 5826-5835.
65. M. Baya, P. Crochet, M. A. Esteruelas, E. Gutiérrez-Puebla, A. M. López, J. Modrego, E. Oñate, N. Vela, Organometallics 2000, 19, 2585-2596.
66. A. J. Andrews, M. A. Esteruelas, F. J. Lahoz, J. Modrego, L. A. Oro, J. Schrickel, Organometallics 1996, 15, 3556-3562.
67. N. Re, A. Sgamellotti, C. Floriani, Organometallics 2000, 19, 1115-1122.
68. V. Cadierno, M. P. Gamasa, J. Gimeno, M. González-Cueva, E. Lastra, J. Borge, S. García-Granda, Organometallics 1996, 15, 2137-2147.
69. M. P. Gamasa, J. Gimeno, C. González-Bernardo, J. Borge, S. García-Granda, Organometallics 1997, 16, 2483-2485.
70. C. González-Bernardo, Ph. D. Thesis, University of Oviedo, 2000.
71. A. Fürstner, M. Picquet, C. Bruneau, P. H. Dixneuf, Chem. Commun. 1998, 1315-1316.
72. Y. Yamamoto, T. Tanase, C. Sudoh, T. Turuta, J. Organomet. Chem. 1998, 569, 29-37.
73. C. Bianchini, N. Mantovani, A. Marchi, L. Marvelli, D. Masi, M. Peruzzini, R. Rossi, A. Romerosa, Organometallics 1999, 18, 4501-4508.
74. M. A. Esteruelas, A. V. Gómez, A. M. López, M. Oliván, E. Oñate, N. Ruiz, Organometallics 2000, 19, 4-14.
75. For related cyclizations using allyl alcohol instead of propargyl alcohol see: M. A. Esteruelas, A. V. Gómez, A. M. López, E. Oñate, N. Ruiz, Organometallics 1998, 17, 2297-2306.
76. D. J. Bernad, M. A. Esteruelas, A. M. López, J. Modrego, M. C. Puerta, P. Valerga, Organometallics 1999, 18, 4995-5003.
77. M. I. Bruce, P. J. Low, E. R. T. Tiekink, J. Organomet. Chem. 1999, 572, 3-10.
78. P. Haquette, D. Touchard, L. Toupet, P. Dixneuf, J. Organomet. Chem. 1998, 565, 63-73.
79. V. Cadierno, M. P. Gamasa, J. Gimeno, M. C. López-González, J. Borge, S. García-Granda, Organometallics 1997, 16, 4453-4463.
80. V. Cadierno, S. Conejero, M. R Gamasa, J. Gimeno, I. Asselberghs, S. Houbrechts, K. Clays, A. Persoons, J. Borge, S. García-Granda, Organometallics 1999, 18, 582-597.
81. V. Cadierno, M. P. Gamasa, J. Gimeno, J. Borge, S. García-Granda, Organometallics 1997, 16, 3178-3187.
82. M. A. Esteruelas, A. V. Gómez, A. M. López, J. Modrego, E. Oñate, Organometallics 1998, 17, 5434-5436.
83. V. Cadierno, M. P. Gamasa, J. Gimeno, J. Chem. Soc., Dalton Trans. 1999, 1857-1866.
84. V. Cadierno, M. P. Gamasa, J. Gimeno, E. Pérez-Carreño, S. García-Granda, Organometallics 1999, 18, 2821-2832.
85. P. Crochet, B. Demerseman, M. I. Vallejo, M. P. Gamasa, J. Gimeno, J. Borge, S. García-Granda, , Organometallics 1997, 16, 5406-5415.
86. V. Cadierno, M. P. Gamasa, J. Gimeno, E. Lastra, J. Chem. Soc., Dalton Trans. 1999, 3235-3243.
87. S. Conejero, M. P. Gamasa, J. Gimeno, unpublished results.
88. V. Cadierno, S. Conejero, M. P. Gamasa, J. Gimeno, J. Chem. Soc., Dalton Trans. 2000, 451-457.
89. 2] are also reported.
90. [62a] V. Cadierno, M. P. Gamasa, J. Gimeno, E. Pérez-Carreño, A. Ienco, Organometallics 1998, 17, 5216-5218. -
91. [62b] V. Cadierno, M. P. Gamasa, J. Gimeno, unpublished results.
92. M. A. Esteruelas, A. V. Gómez, A. M. López, E. Oñate, N. Ruiz, Organometallics 1999, 18, 1606-1614.
93. M. A. Esteruelas, A. V. Gómez, A. M. López, M. C. Puerta, P. Valerga, Organometallics 1998, 17, 4959-4965.
94. [65a] M. A. Esteruelas, A. V. Gómez, A. M. López, E. Oñate, Organometallics 1998, 17, 3567-3573. -
95. [65b] C. Bianchini, M. Peruzzini, R. Rossi, personal communication. -
96. 3, etc.) and thiols (SHPh, SHEt, etc.) to form amino- and thiocarbenes, respectively.
97. B. Buriez, D. J. Cook, K. J. Harlow, A. F. Hill, T. Welton, A. J. P. White, D. J. Williams, J. D. E. T. Wilton-Ely, J. Organomet. Chem. 1999, 575, 264-267.
98. K. J. Harlow, A. F. Hill, T. Welton, J. Chem. Soc., Dalton Trans. 1999, 1911-1912.
99. [4b]
100. M. Laubender, H. Werner, Angew. Chem. Int. Ed. 1998, 37, 150-152.
101. J. Gil-Rubio, B. Weberndörfer, H. Werner, Angew. Chem. Int. Ed. 2000, 39, 786-789.
102. A. Fürstner, B. Gabor, A. F. Hill, L. Jafarpour, M. Liebl, R. Mynott, S. P. Nolan, E. D. Stevens, J. D. E. T. Wilton-Ely, personal communication.
103. K. J. Harlow, A. F. Hill, J. D. E. T. Wilton-Ely, J. Chem. Soc., Dalton Trans. 1999, 285-291.
104. P. Crochet, M. A. Esteruelas, A. M. López, N. Ruiz, J. I. Tolosa, Organometallics 1998, 17, 3479-3486.
105. K. H. Dötz, D. Paetsch, H. Le Bozec, J. Organomet. Chem. 1999, 589, 11-20.
106. M. I. Bruce, B. W. Skelton, A. H. White, N. N. Zaitseva, Inorg. Chem. Commun. 1999, 2, 17-20.
107. R. F. Winter, F. M. Hornung, Organometallics 1999, 18, 4005-4014.
108. R. F. Winter, Chem. Commun. 1998, 2209-2210.
109. R. F. Winter, Eur. J. Inorg. Chem. 1999, 2121-2126. -
110. Related Cope-type rearrangements have been reported with allylic amines. See: R. F. Winter, F. M. Hornung, Organometallics 1997, 16, 4248-4250.
111. M. I. Bruce, M. Ke, B. D. Kelly, P. J. Low, M. E. Smith, B. W. Skelton, A. H. White, J. Organomet. Chem. 1999, 590, 184-201.
112. (Allenylidene)ruthenium(II) complexes have been proposed as key intermediates in the catalytic cyclization-reconstituent addition of propargyl alcohols with allyl alcohols. - [80a] B. M. Trost, J. A. Flygare, J. Am. Chem. Soc. 1992, 114, 5476-5477. -
113. [80b] B. M. Trost, J. A. Flygare, Tetrahedron Lett. 1994, 35, 4059-4062. -
114. [80c] B. M. Trost, Chem. Ber. 1996, 129, 1313-1322.
115. M. Picquet, C. Bruneau, P. H. Dixneuf, Chem. Commun. 1998, 2249-2250.
116. M. Picquet, D. Touchard, C. Bruneau, P. H. Dixneuf, New. J. Chem. 1999, 23, 141-143.
117. A. Fürstner, A. F. Hill, M. Liebl, J. D. E. T. Wilton-Ely, Chem. Commun. 1999, 601-602.
118. Nevertheless, these species show very high catalytic activity, even at room temperature. - [84a] L. Jafarpour, H.-J. Schanz, E. D. Stevens, S. P. Nolan, Organometallics 1999, 18, 5416-5419. -
119. [84b] A. Fürstner, J. Grabowski, C. W. Lehmann, J. Org. Chem. 1999, 64, 8275-8280. -
120. [84c] M. T. Reetz, M. H. Becker, M. Liebl, A. Fürstner, Angew. Chem. Int. Ed. 2000, 39, 1236-1239.
121. M. Saoud, A. Romerosa, M. Peruzzini, Organometallics 2000, 19, 4005-4007.
122. [86a] A. Fürstner, M. Liebl, C. W. Lehmann, M, Picquet, R. Kunz, C. Bruneau, D. Touchard, P. H, Dixneuf, Chem. Eur. J. 2000, 6, 1847-1857. -
123. [86b] A. Fürstner, O. R. Thiel, J. Org. Chem. 2000, 65, 1738-1742.
124. D. J. Bernad, M. A. Esteruelas, A. M. López, M. Oliván, E. Oñate, M. C. Puerta, P. Valerga, Organometallics 2000, 19, 4327-4335.
125. K. Ulrich, E. Porhiel, V. Péron, V. Ferrand, H. Le Bozec, J. Organomet. Chem. 2000, 601, 78-86.
126. K. Ilg, H. Werner, Angew. Chem. Int. Ed. 2000, 39, 1632-1634.
127. S. Szafert, P. Haquette, S. B. Falloon, J. A. Gladysz, J. Organomet. Chem. 2000, 604, 52-58.
128. M. Akita, M. C. Chung, A. Sakurai, Y. Moro-oka, Chem. Commun. 2000, 1285-1286.