Preparation of dinuclear vinylidene complexes and their new deprotonation reactions

Organometallics

Volumn 26, Issue 14, 2007, Pages 3431-3439

  Liu, Chung Wei ^a   Lin, Ying Chih ^a   Huang, Shou Ling ^a   Cheng, Cheng Wei ^a   Liu, Yi Hung ^a   Wang, Yu ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION; DEPROTONATION; ISOMERIZATION; LIGANDS; REACTION KINETICS; VINYL RESINS;

ANCILLARY LIGANDS; BISTRIPHENYLPHOSPHINE LIGANDS; BRIDGING LIGANDS; CARBOCYCLIC RING LIGANDS;

COMPLEXATION;

EID: 34547352136     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om060641o     Document Type: Article

References (109)

1. King, R. B.; Saran, M. S. J. Chem. Soc., Chem. Commun. 1972, 1053.
2. Puerta, M. C.; Valerga, P. Coord. Chem. Rev. 1999, 193-195, 977.
3. (a) Bruce, M. I. Chem. Rev. 1991, 91, 197.
4. (b) Bruce, M. I. Chem. Rev. 1998, 98, 2797.
5. (c) Davies, S. G.; McNally, J. P.; Smallridge, A. J. Adv. Organomet. Chem. 1990, 30, 1.
6. (d) Antonova, A. B. Russ. Chem. Rev. 1989, 58, 693.
7. (a) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 59.
8. (b) Rigaut, S.; Touchard, D.; Dixneuf, P. H. Coord. Chem. Rev. 2004, 248, 1585.
9. (a) Cadierno, V.; Gamasa, M. P.; Gimeno, J. Coord. Chem. Rev. 2004, 248, 1627.
10. (b) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079.
11. (a) Nicolaou, K. Chem. Ber. 1994, 33.
12. (b) Wang, Y.; Finn, M. G. J. Am. Chem. Soc. 1995, 117, 8045.
13. (c) Ohe, K.; Kojima, M.; Yonehara, K.; Uemura, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1823.
14. (a) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311.
15. (b) Bianchini, C.; Frediani, P.; Masi, D.; Peruzzini, M.; Zanobini, F. Organometatlics 1994, 13, 4616.
16. (c) Wakatsuki, Y.; Yamazaki, H.; Kumegava, N.; Satoh, T.; Satoh, J. Y. J. Am. Chem. Soc. 1991, 113, 9604.
17. (d) Yi, C. S.; Liu, N. Synlett 1999, 281.
18. Bruneau, C.; Dixneuf, P. H. Chem. Commun. 1997, 507.
19. (a) Bruneau, C. Top. Organomet. Chem. 2004, 11, 125.
20. (b) Bruneau, C.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2006, 45, 2176.
21. (a) Antonova, A. B.; Ioganson, A. A. Russ. Chem. Rev. 1989, 58, 1197.
22. (b) Werner, H. J. Organomet. Chem. 1994, 475, 45.
23. (c) Werner, H. Chem. Commun. 1997, 903.
24. (d) Werner, H. Coord. Chem. Rev. 2004, 248, 1693.
25. (e) Valyaev, D. A.; Semeikin, O. V.; Ustynyuk, N. A. Coord. Chem. Rev. 2004, 248, 1679.
26. (f) Selegue, J. P. Coord. Chem. Rev. 2004, 248, 1543.
27. (g) Bruce, M. I. Coord. Chem. Rev. 2004, 248, 1603.
28. (h) Herndon, J. W. Coord. Chem. Rev. 2004, 248, 3.
29. (a) Creutz, C. Prog. Inorg. Chem. 1983, 30, 1.
30. (b) Astruc, D. Electron Transfer and Radical Processes in Transition Metal Chemistry; VCH: New York, 1995.
31. (c) Nelsen, S. F. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, Chapter 10.
32. (d) Launay, J.-P.; Coudret, C. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 5, Chapter 1.
33. (e) Launay, J.-P. Chem. Soc. Rev. 2001, 30, 386.
34. (f) Demadis, K. D.; Hartshorn, C. M.; Meyer, T. J. Chem. Rev. 2001, 101, 2655.
35. (g) Brunschwig, B. S.; Creutz, C.; Sutin, N. Chem. Soc. Rev. 2002, 31, 168.
36. (a) Cotton, F. A.; Liu, C. Y.; Murillo, C. A.; Villagrán, D.; Wang, X. J. Am. Chem. Soc. 2004, 126, 14822.
37. (b) Kar, S.; Sarkar, B.; Ghumaan, S.; Janardanan, D.; van Siegeren, J.; Fielder, J.; Puranik, V. G.; Sunoj, R. B.; Kaim, W.; Lahiri, G. K. Chem.-Eur. J. 2005, 11, 4901.
38. (a) Paul, F.; Lapinte, C. In Unusual Structures and Physical Properties in Organometallic Chemistry; Gielen, M., Willem, R., Wrackmeyer, B., Eds.; Wiley: New York, 2002; p 220.
39. (b) Szafert, S.; Gladysz, J. A Chem. Rev. 2003, 103, 4175.
40. (c) Bruce, M. I.; Low, P. J. Adv. Organomet. Chem. 2004, 50, 179.
41. (d) Antonova, A. B.; Bruce, M. I.; Ellis, B. G.; Gaudio, M.; Humphrey, P. A.; Jevric, M.; Melino, G.; Nicholson, B. K.; Perkins, G. J.; Skelton, B. W.; Stapleton, B.; White, A. H.; Zaitseva, N. N. Chem. Commun. 2004, 960.
42. (e) Roue, S.; Lapinte, C.; Bataille, T. Organometallics 2004, 23, 2558.
43. (f) de Montigny, F.; Argouarch, G.; Costuas, K.; Halet, J.-F.; Roisnel, T.; Toupet, L.; Lapinte, C. Organometallias 2005, 24, 4558.
44. (g) Bruce, M. I.; Costuas, K.; Davin, T.; Ellis, B. G.; Halet, J.-F.; Lapinte, C.; Low, P. J.; Smith, M. E.; Skelton, B. W.; Toupet, L.; White, A. H. Organometallics 2005, 24, 3864.
45. (a) Sakurai, A.; Akita, M.; Moro-oka, Y. Organometallics 1999, 18, 3241.
46. (b) Dembinski, R.; Bartik, T.; Bartik, B.; Jaeger, M.; Gladysz, J. A. J. Am. Chem. Soc. 2000, 122, 810.
47. (c) Stahl, J.; Bohling, J. C.; Bauer, E. B.; Peters, T. B.; Mohr, W.; Martin-Alvarez, J. M.; Hampel, F.; Gladysz, J. A. Angew. Chem., Int. Ed. 2002, 41, 1872.
48. (d) Owen, G. R.; Hampel, F.; Gladysz, J. A, Organometallics 2004, 23, 5893.
49. (e) Zhuravlev, F.; Gladysz, J. A. Chem.-Eur. J. 2004, 10, 6510.
50. (f) Owen, G. R.; Stdahl, J.; Hampel, F.; Gladysz, J. A. Organometallics 2004, 23, 5889.
51. (g) Zheng, Q.; Gladysz, J. A. J. Am. Chem. Soc. 2005, 127, 10508.
52. (a) Hartbaum, C.; Mauz, E.; Roth, G.; Weissenbach, K.; Fischer, H. Organometallics 1999, 18, 2619.
53. (b) Fernandez, F. J.; Blacque, O.; Alfonso, M.; Berke, H. Chem. Commun. 2000, 1266.
54. (c) Gil-Rubio, J.; Werberndorfer, B.; Werner, H. Angew. Chem., Int. Ed. 2000, 39, 786.
55. (d) Wong, K. T.; Lehn, J.-M.; Peng, S.-M.; Lee, G.-H. Chem. Commun. 2000, 2259.
56. (e) Fernandez, F. J.; Kheradmandan, S.; Venkatesan, K.; Blacque, O.; Alfonso, M.; Schmalle, H. W.; Berke, H. Chem.-Eur. J. 2003, 9, 6192.
57. (f) Kheradmandan, S.; Venkatesan, K.; Blacque, O.; Schmalle, H. W.; Berke, H. Chem.-Eur. J. 2004, 10, 4872.
58. (g) Rigaut, S.; Touchard, D.; Dixneuf, P. H. Coord. Chem. Rev. 2004, 1586.
59. (h) Ren, T. Organometallics 2005, 24, 4854.
60. Liu, S. H.; Hu, Q. Y.; Xue, P.; Wen, T. B.; Williams, I. D.; Jia, G. Organometallics 2005, 24, 769.
61. (a) Ziessel, R.; Hissler, M.; El-ghaoury, A.; Harriman, A. Coord. Soc. Rev. 1998, 178-180, 1251.
62. (b) Welter, K.; Brunner, J.; Hofstraat, W.; De Cola, L. Nature 2003, 21, 54.
63. (c) Baranof, E.; Collin, J.-P.; Flamini, L.; Sauvage, J.-P. Chem. Chem. Rev. 2004, 33, 147.
64. (d) Hofmeier, H.; Shubert, U. S. Chem. Soc. Rev. 2004, 33, 373.
65. (a) Etzenhouser, B. A.; Chen, Q.; Sponsler, M. B. Organometallics 1994, 13, 4176.
66. (b) Lehn, J.-M. Supramolecular Chemistry-Concepts and Perspectives; VCH: Weinheim, 1995.
67. (c) Tour, J. M. Chem. Rev. 1996, 96, 537.
68. (d) Atomic and Molecular Wires; Joachim, C., Roth, S., Eds.; Kluwer: Dordrecht, The Netherlands, 1997.
69. (e) McCleverty, J. A.; Ward, M. D. Acc. Chem. Res. 1998, 31, 842.
70. (f) Schwab, R. F. H.; Levin, M. D.; Michl, J. Chem. Rev. 1999, 99, 1863.
71. (g) Chung, M.-C.; Gu, X.; Etzenhouser, B. A.; Spuches, A. M.; Rye, P. T.; Seetharaman, S. K.; Rose, D. J.; Zubieta, J.; Sponsler, M. B. Organometallics 2003, 22, 3485.
72. (h) Cotton, F. A.; Donahue, J. P.; Murillo, C. A. J. Am. Chem. Soc. 2003, 125, 5436.
73. (i) Diketo, B.; Hoshino, Y.; Higushi, S.; Fielder, J.; Su, C.-Y.; Knolder, A.; Schwederski, B.; Sarkar, B.; Hartmann, H.; Kaim, W. Angew. Chem., Int. Ed. 2003, 43, 674.
74. (a) Lu, W.; Xiang, H.-F.; Zhu, N.; Che, C.-M. Organometallics 2002, 21, 2343.
75. (b) Yam, V. W.-W.; Wong, K. M.-C.; Zhu, N. Angew. Chem., Int. Ed. 2003, 43, 1400.
76. Ung, V. A.; Cargill, W.; Thompson, A. M.; Bardwell, D. A.; Gatteschi, D.; Jeffery, J. C.; McCleverty, J. A.; Tolti, F.; Ward, M. D. Inorg. Chem. 1997, 36, 3447.
77. (a) Senechal, K.; Maury, O.; Le Bozec, H.; Ledoux, I.; Zyss, J. J. Am. Chem. Soc. 2002, 124, 4560.
78. (b) Powell, C. E.; Humphrey, M. G. Coord. Chem. Rev. 2004, 248, 725.
79. (c) Fillaut, J.-L.; Perruchon, J.; Blanchard, P.; Roncali, J.; Golhen, S.; Allain, M.; Migalsaka-Zalas, A.; Kityk, I. V.; Sahraoui, B. Organometallics 2005, 24, 687.
80. Qi, H.; Gupta, A.; Noll, B. C.; Snider, G. L.; Lu, Y.; Lent, C.; Fehlner, T. P. J. Am. Chem. Soc. 2005, 127, 15218.
81. (a) Ting, P. C.; Lin, Y. C.; Cheng, M. C.; Wang, Y. Organometallics 1994, 13, 2150.
82. (b) Ting, P. C.; Lin, Y. C.; Lee, G. H.; Cheng, M. C.; Wang, Y. J. Am. Chem. Soc. 1996, 118, 6433.
83. (c) Chang, C. W.; Ting, C. P.; Lin, Y. C.; Lee, G. H.; Wang, Y. J. Organomet. Chem. 1998, 553, 417.
84. (d) Chang, K. H.; Lin, Y. C. Chem. Commun. 1998, 1441.
85. (e) Lo, Y. H.; Lin, Y. C.; Lee, G. H.; Wang, Y. Organometallics 1999, 18, 982.
86. (f) Chang, C. W.; Lin, Y. C.; Lee, G. H.; Wang, Y. Organometallics 2000, 19, 3211.
87. (g) Chang, K. H.; Lin, Y. C.; Liu, Y. H.; Wang, Y. J. Chem. Soc., Dalton Trans. 2001, 3154.
88. (h) Huang, C. C.; Lin, Y. C.; Liu, Y. H.; Wang, Y. Organometallics 2003, 22, 1512.
89. Yen, Y. S.; Lin, Y. C.; Huang, S. L.; Liu, Y. H.; Sung, H. L.; Wang, Y. J. Am. Chem. Soc. 2005, 127, 18037.
90. (a) Rigaut, S.; Le Pichon, L.; Daran, J.-C.; Touchard, D.; Dixneuf, P. H. Chem. Commun. 2001, 1206.
91. (b) Rigaut, S.; Massue, J.; Touchard, D.; Fillaut, J.-L.; Golhen, S.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2002, 47, 4513.
92. (a) Weng, W. J.; Berenguer, R.; Fornies, J.; Lalind, E.; Martinez, F.; Sanchez, L.; Serrano, B. Organometallics 1998, 17, 1640.
93. (b) Roth, G.; Reindl, D.; Gockel, M.; Troll, C.; Fischer, H. Organometallics 1998, 17, 1393.
94. (c) Leroux, F.; Stumph, R.; Fischer, H. Eur. J. Inorg. Chem. 1998, 1225.
95. (d) Dembinski, R.; Szafert, S.; Haquette, P.; Lis, T.; Gladysz, J. A. Organometallics 1999, 18, 5438.
96. (e) Xia, H. P.; Ng, W. S.; Ye, J. S.; Li, X. Y.; Wong, W. T.; Lin, Z.; Yang, C.; Jia, G. Organometallics 1999, 18, 4552.
97. (f) Hartbaum, C.; Fischer, H. J. Organomet. Chem. 1999, 578, 186.
98. (g) Fuss, B.; Dede, M.; Weibert, B.; Fischer, H. Organometallics 2002, 21, 4425.
99. (a) Connelly, N. G.; Gamasa, M. P.; Gimeno, J.; Lapinet, C.; Lastra, E.; Maher, J. P.; Le Narvor, N.; Rieger, A. L.; Rieger, P. H. J. Chem. Soc., Dalton Trans. 1993, 2575.
100. (b) Bitcon, C.; Whitely, M. W. J. Organomet. Chem. 1987, 336, 385.
101. (a) Hill, A. F.; Hulkes, A. G.; White, A. J. P.; Williams, D. J. Organometallics 2000, 19, 371.
102. (b) Bruce, M. I.; Ellis, B. G.; Low, P. J.; Skelton, B. W.; White, A. H. Organometallics 2003, 22, 3184.
103. (a) Bruce, M. I.; Ellis, B. G.; Gaudio, M.; Lapinte, C.; Melino, G.; Paul, F.; Skelton, B. W.; Smith, M. E.; Toupet, L.; White, A. H. Dalton Trans. 2004, 1601.
104. (b) Bruce, M. I.; Hall, B. C.; Kelly, B. D.; Low, P. J.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1999, 3719.
105. (a) Tadeusz, W.; Maria, B.; Biernat, J. F. J. Organomet. Chem. 1981, 215, 87.
106. (b) Goto, A.; Tenorio, M. J.; Puerta, M. C.; Valerga, P. Organometallics 1998, 17, 4392.
107. (c) Bruce, M. I.; Wallis, R. C. Aust. J. Chem. 1979, 32, 1471.
108. The SADABS program is based on the method of Blessing; see: Blessing, R. H. Acta Crystallogr., Sect. A 1995, 51, 33.
109. SHELXTL, Structure Analysis Program, version 5.04; Siemens Industrial Automation Inc.: Madison, WI, 1995.