Novel ruthenium complex-catalyzed dimerization of 2,5-norbornadiene to pentacyclo[6.6.0.02,6.03,13.010,14]tetradeca-4,11-diene involving carbon-carbon bond cleavage

Journal of the American Chemical Society

Volumn 121, Issue 9, 1999, Pages 1839-1850

  Mitsudo, Take Aki ^a   Suzuki, Toshiaki ^a   Zhang, Shi Wei ^a,b   Imai, Daisuke ^a   Fujita, Ken Ichi ^a   Manabe, Takao ^a   Shiotsuki, Masashi ^a   Watanabe, Yoshihisa ^a   Wada, Kenji ^a   Kondo, Teruyuki ^a  

^a KYOTO UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CATALYSIS; CHEMICAL BONDS; DERIVATIVES; DIMERS; MOLECULES; OLEFINS; X RAY ANALYSIS;

HEPTACYCLOTETRADECANE; NORBORNADIENE; TETRAHYDROFURAN;

RUTHENIUM;

ALKADIENE; ALKENE DERIVATIVE; DIMETHYL SULFOXIDE; FUMARIC ACID DIMETHYL ESTER; NORBORNADIENE DERIVATIVE; RUTHENIUM COMPLEX; SOLVENT; TETRAHYDROFURAN; TOLUENE;

ARTICLE; CATALYSIS; CATALYST; CRYSTAL STRUCTURE; DIMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033541142     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9835741     Document Type: Article

References (154)

1. For reviews, see: (a) Bishop, K. C. Chem. Rev. 1976, 76, 461. (b) Crabtree, R. H. Chem. Rev. 1985, 55, 245. (c) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241.
2. For reviews, see: (a) Bishop, K. C. Chem. Rev. 1976, 76, 461. (b) Crabtree, R. H. Chem. Rev. 1985, 55, 245. (c) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241.
3. For reviews, see: (a) Bishop, K. C. Chem. Rev. 1976, 76, 461. (b) Crabtree, R. H. Chem. Rev. 1985, 55, 245. (c) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241.
4. (a) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780.
5. (b) Noyori, R.; Kumagai, Y.; Umeda, I.; Takaya, H. J. Am. Chem. Soc. 1972, 94, 4018.
6. (a) Aoki, S.; Fujimura, T.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1988, 110, 3296.
7. (b) Fujimura, T.; Aoki, S.; Nakamura, E. J. Org. Chem. 1991, 56, 2809.
8. (a) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Jones, W. D. Organometallics 1997, 16, 2013.
9. (b) Edelbach, B. L.; Lachicotte, R. J.; Jones, W. D. J. Am. Chem. Soc. 1998, 120, 2843.
10. Lautens, M.; Ren, Y. J. Am. Chem. Soc. 1996, 118, 10668.
11. Kaneda, K.; Azuma, H.; Wayaku, M.; Teranisi, S. Chem. Lett. 1974, 215.
12. Suggs, J. W.; Jun, C.-H. Chem. Commun. 1985, 92.
13. Lieu, S.-Y.; van der Boom, M.; Milstein, D. Chem. Commun. 1998, 687.
14. (a) Huffman, M. A.; Liebeskind, L. S. J. Am. Chem. Soc. 1991, 113, 2771.
15. (b) Huffman, M. A.; Liebeskind, L. S. J. Am. Chem. Soc. 1993, 115, 4895.
16. (a) Murakami, M.; Amii, H.; Ito, Y. Nature 1994, 370, 540.
17. (b) Murakami, M.; Amii, H.; Shigeto, K.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 8285.
18. (c) Murakami, M.; Takahashi, K.; Amii, H.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 9307.
19. (d) Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, I.; Ito, Y. J. Org. Chem. 1998, 63, 4.
20. Hayashi, M.; Ohmatsu, T.; Meng, Y.-P.; Saigo, K. Angew. Chem., Int. Ed. Engl. 1998, 37, 837.
21. (a) Rondon, D.; Chaudret, B.; He, X.-D.; Labroue, D. J. Am. Chem. Soc. 1991, 113, 5671.
22. (b) Perthuisot, C.; Jones, W. D. J. Am. Chem. Soc. 1994, 116, 3647.
23. Harayama, H.; Kuroki, T.; Kimura, M.; Tanaka, S.; Tamaru, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 2352.
24. Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123.
25. Kondo, T.; Kodoi, K.; Nishinaga, E.; Okada, T.; Morisaki, Y.; Watanabe, Y.; Mitsudo, T. J. Am. Chem. Soc. 1998, 120, 5587.
26. Nokami, J.; Yoshizane, K.; Matsuura, H.; Sumida, S. J. Am. Chem. Soc. 1998, 120, 6609.
27. Bennett, M. A.; Matheson, T. W. In Comprehensive Organometallic Chemistry; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U. K., 1982; Vol. 4, p 931.
28. (a) Trost, B. M.; Krause, L.; Portnoy, M. J. Am. Chem. Soc. 1997, 119, 11319.
29. (b) Trost, B. M.; Portnoy, M.; Kurihara, H. J. Am. Chem. Soc. 1997, 119, 836.
30. (c) Trost, B. M.; Imi, K.; Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371.
31. (d) Trost, B. M.; Mueller, T. J. J.; Martines, J. J. Am. Chem. Soc. 1995, 117, 1888.
32. (e) Trost, B. M.; Indolese, A. F.; Mueller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615.
33. (f) Trost, B. M.; Mueller, T. J. J. J. Am. Chem. Soc. 1994, 116, 4985.
34. (g) Trost, B. M.; Flygare, J. A. J. Org. Chem. 1994, 59, 1078.
35. (h) Trost, B. M.; Martines, J.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 10402.
36. (i) Trost, B. M.; Imi, K.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 8831.
37. (j) Trost, B. M.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 4361.
38. (a) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335.
39. (b) Fukuyama, T.; Chatani, N.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 5647.
40. (c) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762.
41. (d) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 2604.
42. (e) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493.
43. (f) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049.
44. (g) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
45. (a) Yamamoto, Y.; Kitahara, H.; Hattori, R.; Itoh, K. Organometallics 1998, 17, 1910.
46. (b) Itoh, K.; Masuda, K.; Fukahori, T.; Nakano, K.; Aoki, K.; Nagashima, H. Organometallics 1994, 13, 1020.
47. (c) Masuda, K.; Ohkita, H.; Kurumatani, S.; Itoh, K. J. Organomet. Chem. 1993, 454, C13.
48. (d) Masuda, K.; Ohkita, H.; Kurumatani, S.; Itoh, K., Organometallics 1993, 12, 2221.
49. (a) Doyle, M. P.; Peterson, C. S.; Zhou, Q.-L.; Nishiyama, H. Chem. Comuun. 1997, 211.
50. (b) Park, S.-B.; Murata, K.; Matsumoto, H.; Nishiyama, H. Tetrahedron: Assym. 1995, 6, 2487.
51. (c) Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
52. (a) Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887.
53. (b) Kim, S. H.; Zuercher, W. J.; Bowden, N. B.; Grubbs, R. H. J. Org. Chem. 1996, 61, 1073.
54. (c) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039.
55. (d) Fu, G. C.; Grubbs, R. H.; Nguyen, S. T. J. Am. Chem. Soc. 1993, 115, 9856.
56. (e) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858.
57. (a) Kinoshita, A.; Mori, M. Heterocycles 1997, 46, 287.
58. (b) Kinoshita, A.; Sakakibara, N.; Mori, M. J. Am. Chem. Soc. 1997, 119, 12388.
59. (c) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356.
60. (d) Kinoshita, A.; Mori, M. Synlett. 1994, 12, 1020.
61. (a) Mitsudo, T.; Naruse, H.; Kondo, T.; Ozaki, Y.; Watanabe, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 580.
62. (b) Mitsudo, T.; Nakagawa, Y.; Watanabe, K.; Hori, Y.; Masawa, H.; Watanabe, H.; Watanabe, Y. J. Org. Chem. 1985, 50, 565.
63. (c) Mitsudo, T.; Nakagawa, Y.; Watanabe, H.; Watanabe, K.; Masawa, H.; Watanabe, Y. Chem. Commun. 1981, 496.
64. (a) Mitsudo, T.; Zhang, S.-W.; Nagao, M.; Watanabe, Y. Chem. Commun. 1991, 598.
65. (b) Mitsudo, T.; Hori, Y.; Watanabe, Y. J. Organomet. Chem. 1987, 334, 157.
66. (c) Mitsudo, T.; Hori, Y.; Watanabe, Y. Bull. Chem. Soc. Jpn. 1986, 59, 3201.
67. (d) Mitsudo, T.; Kokuryo, K.; Shinsugi, T.; Nakagawa, Y.; Watanabe, Y.; Takegami, Y. J. Org. Chem. 1979, 44, 4492.
68. (a) Zhang, S.-W.; Mitsudo, T.; Kondo, T.; Watanabe, Y. J. Organomet. Chem. 1995, 485, 55.
69. (b) Zhang, S.-W.; Mitsudo, T.; Kondo, T.; Watanabe, Y. J. Organomet. Chem. 1993, 450, 197.
70. (c) Mitsudo, T.; Zhang, S.-W.; Kondo, T.; Watanabe, Y. Tetrahedron Lett. 1992, 33, 341.
71. (d) Mitsudo, T.; Zhang, S.-W.; Satake, N.; Kondo, T.; Watanabe, Y. Tetrahedron Lett. 1992, 33, 5533.
72. (e) Mitsudo, T.; Takagi, M.; Zhang, S.-W.; Watanabe, Y. J. Organomet. Chem. 1992, 423, 405.
73. (a) Suzuki, N.; Kondo, T.; Mitsudo, T. Organometallics 1998, 17, 766.
74. (b) Kondo, T.; Suzuki, N.; Okada, T. Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187.
75. Mitsudo, T.; Zhang, S.-W.; Watanabe, Y. Chem. Commun. 1994, 435.
76. Lemal, D. M.; Shim, K. S. Tetrahedron Lett. 1961, 11, 368.
77. Bird, C. W.; Colinese, D. L.; Cookson, R. C.; Hudec, J.; Williams, R. O. Tetrahedron Lett. 1961, 11, 373.
78. Jolly, P. W.; Stone, F. G. A.; Mackenzie, K. J. Chem. Soc. 1965, 6416.
79. Langenbach, H. J.; Keller, E.; Vahrenkamp, H. Angew. Chem., Int Ed. Engl. 1977, 16, 188.
80. (a) Ennis, M.; Manning, A. R. J. Organomet. Chem. 1976, 116, C31.
81. (b) Ennis, M.; Foley, R. M.; Manning, A. R. J. Organomet. Chem. 1979, 166, C18.
82. (a) Schrauzer, G. N.; Bastian, B. N.; Fosselius, G. A. J. Am. Chem, Soc. 1966, 88, 4890.
83. (b) Schrauzer, G. N.; Ho, R. K. Y.; Schlesinger, G. Tetrahedron Lett. 1970, 543.
84. Arnold, D. R.; Trecker, D. J.; Whipple, E. B. J. Am. Chem. Soc. 1965, 87, 2596.
85. Kanai, H.; Watabe, Y.; Nakayama. T. Bull. Chem. Soc. Jpn. 1986, 59, 1277.
86. (a) Mrowca, J. J.; Katz, T. J. J. Am. Chem. Soc. 1966, 88, 4012.
87. (b) Katz, T. J.; Carnahan Jr., J. C.; Boecke, R. J. Org. Chem. 1967, 32, 1301.
88. (c) Acton, N.; Roth, R. J.; Katz, T. J.; Frank, J. K.; Maier, C. A.; Paul, I. C. J. Am. Chem. Soc. 1972, 94, 5446.
89. Kiji, J.; Nishimura, S.; Yoshikawa, S.; Sasakawa, E.: Furukawa, J. Bull. Chem. Soc. Jpn. 1974, 47, 2523.
90. (a) Bird, C. W.; Cookson, R. C.; Hudec, J. Chem. Ind. 1960, 20.
91. (b) Doyle, M. J.; McMeeking, J.; Binger, P. Chem. Commun. 1976, 376.
92. Voecks, G. E.; Jennings, P. W.; Smith, G. D.; Caughlan, C. N. J. Org. Chem. 1972, 37, 1460.
93. Yoshikawa, S.; Kiji, J.; Furukawa, J. Bull. Chem. Soc. Jpn. 1976, 49, 1093.
94. (a) Chow, T. J.; Chao, Y.-S.; Liu, L.-K. J. Am. Chem. Soc. 1987, 109, 797.
95. (b) Chow, T. J.; Chao, Y.-S. J. Chem. Commun. 1985, 700.
96. (c) Chow, T. J.; Chao, Y.-S. J. Organomet. Chem. 1985, 296, C23.
97. (d) Chow, T. J.; Wu, M.-Y.; Liu, L.-K. J. Organomet. Chem. 1985, 281, C33.
98. Frosin, K.-M.; Dahlenburg, L. Inorg. Chim. Acta 1990, 167, 83.
99. (a) Pertici, P.; Vitulli, G.; Lazzaroni, R.; Salvadori, P. J. Chem. Soc., Dalton Trans. 1982, 1019.
100. (b) Vitulli, G.; Pertici, P.; Salvadori, P. J. Chem. Soc., Dalton Trans. 1984, 2255.
101. (c) Vitulli, G.; Pertici, P.; Bigelli, C. Gazzetta Chim. Ital. 1985, 115, 79.
102. (d) Vitulli, G.; Bertozzi, S.; Lazzaroni, R. Inorg. Chim. Acta 1988, 149, 235.
103. Deganello, G.; Mantovani, A.; Sandrini, P. L.; Pertici, P.; Vitulli, G.J. Organomet. Chem. 1977, 135, 215.
104. (a) Chaudret, B.; Commenges, G.; Poilblanc, R. Chem. Commun. 1982, 1388.
105. (b) Chaudret, B.; Commenges, G.; Poilbanc, R. J. Chem. Soc., Dalton Trans. 1984, 1635.
106. Pertici, P.; Vitulli, G.; Porzio, W.; Zocchi, M.; Barili, P. L.; Deganello, G. J. Chem. Soc., Dalton Trans. 1983, 1553.
107. Hirano, M.; Marumo, T.; Miyasaka, T.; Fukuoka, A.; Komiya, S. Chem. Lett. 1997, 297.
108. (a) Marchand, A. P. J. Org. Chem. 1984, 49, 1660.
109. (b) Marchand, A. P.; Hayes, B. R. Tetrahedron Lett. 1977, 1027.
110. (a) Suzuki, H.; Kakigano, T.; Fukui, H.; Tanaka, M.; Moro-oka, Y. J. Organomet. Chem. 1994, 473, 295.
111. (b) Kakigano, T.; Suzuki, H.; Igarashi, M.; Moto-oka, Y. Organometallics 1990, 9, 2192.
112. Bennett, M. A.; Nicholls, J. C.; Rahman, A. K. F.; Redhouse, A. D.; Spencer, J. L.; Willis, A. C. Chem. Commun. 1989, 1328.
113. Ito, K.; Oshima, N.; Jameson, G. B.; Lewis, H. C.; Ibers, J. A. J. Am. Chem. Soc. 1981, 103, 3014.
114. 3CN (ref 52) was not an active catalyst for the dimerization of 1a to 2a. These facts suggest that a neutral complex without a halogen ligand is a catalytically active species.
115. (a) Kondo, T.; Hiraishi, N.; Morisaki, Y.; Wada, K.; Watanabe, Y.; Mitsudo, T. Organometallics 1998, 17, 2131.
116. (b) Watanabe, Y.; Morisaki, Y.; Kondo, T.; Mitsudo, T. J. Org. Chem. 1996, 61, 4214.
117. (c) Mitsudo, T.; Suzuki, N.; Kondo, T.; Watanabe, Y. J. Org. Chem. 1994, 59, 7759.
118. (d) Kondo, T.; Akazome, M.; Tsuji, Y.; Watanabe, Y. J. Org. Chem. 1990, 55, 1286.
119. (e) Hori, Y.; Mitsudo, T.; Watanabe, Y. Bull. Chem. Soc. Jpn. 1988, 61, 3011.
120. (f) Hori, Y.; Mitsudo, T.; Yamakawa, Y.; Watanabe, Y. J. Organomet. Chem. 1987, 321, 397.
121. (g) Kondo, T.; Tsuji, Y.; Watanabe, Y. Tetrahedron Lett. 1987, 28, 6229.
122. (h) Mitsudo, T.; Hori, Y.; Yamakawa, Y.; Watanabe, Y. Tetrahedron Lett. 1987, 28, 4417.
123. (i) Tsuji, Y.; Huh, Keun Tae; Ohsugi, Y.; Watanabe, Y. J. Org. Chem. 1985, 50, 1365.
124. (a) Fukuoka, A.; Nagano, T.; Furuta, S.; Yoshizawa, M.; Hirano, M.; Komiya, S. Bull. Chem. Soc. Jpn. 1998, 71, 1409.
125. (b) Ohgomori, Y.; Ichikawa, S.; Sumitani, N. Organometallics 1994, 13, 3758.
126. (c) Maruyama, Y.; Sezaki, T.; Tekawa, M.; Sakamoto, T.; Shimizu, I.; Yamamoto, A. J. Organomet. Chem. 1994, 473, 257.
127. (d) Wakatsuki, Y.; Yamazaki, H.; Kumegawa, N.; Satoh, J. Y. J. Am. Chem. Soc. 1991, 113, 9604.
128. (e) Wakatsuki, Y.; Yamazaki, H.; Kumegawa, N.; Johar, P. S. Bull. Chem. Soc. Jpn. 1993, 66, 987.
129. (f) Airoldi, M.; Deganello, G.; Dia, G.; Gennaro, G. Inorg. Chim Acta 1983, 68, 179.
130. (g) Pertici, P.; Vitulli, G.; Carlini, C. J. Mol. Catal. 1981, 11, 353.
131. (h) Airoldi, M.; Deganello, G.; Dia, G.; Gennaro, G. J. Organomet. Chem. 1980, 187, 391.
132. (a) Itoh, K.; Nagashima, H.; Ohshima, T.; Oshima, N.; Nishiyama, H. J. Organomet. Chem. 1984, 272, 179.
133. (b) Pertici, P.; Vitulli, G. J. Chem. Soc., Dalton. Trans. 1980, 1961.
134. Hallman, P. S.; Stephenson, T. A.; Wilkinson, G. Inorg. Synth. 1970, 12, 237.
135. Young, R.; Wilkinson, G. Inorg, Synth. 1977, 17, 75.
136. Parshall, G. W. Inorg. Synth. 1974, 15, 48.
137. Oshima, N.; Suzuki, H.; Moro-oka, Y. Chem. Lett. 1984, 1161.
138. Nelson, G. O.; Summer, C. E. Organometallics 1986, 5, 1983.
139. Humphries, A.; Knox, S. A. R. J. Chem. Soc., Dalton Trans. 1975, 1710.
140. Mantovani, A.; Cenini, S. Inorg. Synth. 1976, 16, 51.
141. Bennett, M. A.; Wilkinson, G. Chem. Ind. 1959, 1516.
142. Keister, J. B.; Shapley, J. B.; Strickland, D. A. Inorg. Synth. 1990, 27, 196.
143. Lavigne, G.; Kaesz, H. D. J. Am. Chem. Soc. 1984, 106, 4647.
144. Coulson, D. R. Inorg. Synth. 1972, 13, 121.
145. Osborn, J. A.; Wilkinson, G. Inorg. Synth. 1967, 10, 67.
146. Burch, R. R.; Muetterties, E. L.; Day, V. W. Organometallics 1982, 1, 188.
147. Maitlis, P. M.; Kang, J. W.; Moseley, K. J. J. Chem Soc. A 1970, 2875.
148. Story, P. R. J. Org. Chem. 1961, 26, 287.
149. Story, P. R.; Fahrenholtz, S. R. J. Org. Chem. 1963, 28, 1716.
150. SHELX86: Sheldrick, G. M. Crystallographic Computing 3; Sheldrick, G. M.; Kruger, C.; Goddard, R.; Eds.; Oxford University Press: Oxford, U. K., 1985; pp 175-189.
151. (a) Cromer, D. T.; Waber, G. T. International Tables for X-ray Crystallography; Kynoch: Birmingham, U.K., 1974; Vol. IV.
152. (b) Ibers, J. A.; Hamilton, W. C. Acta Crystallogr. 1964, 17, 781.
153. (c) Creagh, D. C.; McAuley, W. J. International Tables for X-ray Crystallography; Wilson, A. J. C., Ed.; Kluwer Academic Publishers: Boston, MA, 1992; Vol. C.
154. teXsan: Crystal Structure Analysis Package; Molecular Structure Corp.: The Woodlands, TX, 1985, 1992.