Organic reactions catalyzed by rhenium carbonyl complexes

Chemical Reviews

Volumn 111, Issue 3, 2011, Pages 1938-1953

  Kuninobu, Yoichiro ^a   Takai, Kazuhiko ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC AMOUNTS; CH-BOND ACTIVATION; CYCLOPENTADIENES; DI-ENOL; DIHYDROGEN; FRIEDEL-CRAFTS ACYLATION; OLEFIN METATHESIS; ORGANIC REACTION; RHENIUM CARBONYL COMPLEXES; RHENIUM COMPLEXES; SILYL ETHERS; TANDEM CYCLIZATION;

CARBONYLATION; CARBOXYLIC ACIDS; CATALYSIS; CATALYSTS; CYCLIZATION; ETHERS; OLEFINS; RHENIUM;

RHENIUM COMPOUNDS;

EID: 79952689970     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr100241u     Document Type: Review

References (159)

1. Boag, N. M.; Kaesz, H. D. Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Vol. 4, pp 161-242.
2. O'Connor, J. M. Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 6, pp 167-229.
3. Hoffman, D. M. Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 6, pp 231-255.
4. Romão, C. C.; Royo, B. Comprehensive Organometallic Chemistry III; Crabtree, R. H., Mingos, D. M. P., Eds.; Elsevier: Amsterdam, the Netherlands, 2007; Vol. 5, pp 855-960.
5. Herrmann, W. A. J. Organomet. Chem. 1995, 500, 149
6. Herrmann, W. A.; Kühn, F. E. Acc. Chem. Res. 1997, 30, 169
7. Espenson, J. H. Adv. Inorg. Chem. 2003, 54, 157
8. Kühn, F. E.; Santos, A. M.; Herrmann, W. A. Dalton Trans. 2005, 2483
9. There have been a few reviews of rhenium-catalyzed transformations. See
10. Kusama, H.; Narasaka, K. J. Synth. Org. Chem. Jpn. 1996, 54, 644
11. Hua, R.; Jiang, J.-L. Curr. Org. Synth. 2007, 4, 151
12. Harris, G. W.; Boeyens, J. C. A.; Coville, N. J. J. Chem. Soc., Dalton Trans. 1985, 2277
13. Ingham, W. L.; Coville, N. J. J. Organomet. Chem. 1992, 423, 51
14. Harris, G. W.; Coville, N. J. Organometallics 1985, 4, 908
15. Harris, G. W., Boeyens, J. C. A., and Coville, N. J. Organometallics 1985, 4, 914
16. Hileman, J. C.; Huggins, D. K.; Kaesz, H. D. Inorg. Chem. 1962, 1, 933
17. Kaesz, H. D. J. Organomet. Chem. 1980, 200, 145
18. George, M. W.; Johnson, F. P. A.; Westwell, J. R.; Hodges, P. M.; Turner, J. J. J. Chem. Soc., Dalton Trans. 1993, 2977
19. Rossenaar, B. D.; Stufkens, D. J.; Vlček, A., Jr. Inorg. Chem. 1996, 35, 2902
20. Chen, H.; Hartwig, J. F. Angew. Chem., Int. Ed. 1999, 38, 3391
21. Kuninobu, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2005, 127, 13498
22. Kusama, H.; Narasaka, K. Bull. Chem. Soc. Jpn. 1995, 68, 2379
23. Nishiyama, Y.; Kakushou, F.; Sonoda, N. Bull. Chem. Soc. Jpn. 2000, 73, 2779
24. Hua, R.; He, J.; Sun, H. Chin. J. Chem. 2007, 25, 132
25. Kuninobu, Y.; Matsuki, T.; Takai, K. J. Am. Chem. Soc. 2009, 131, 9914
26. Hirano, M.; Hirai, M.; Ito, Y.; Tsurumaki, T.; Baba, A.; Fukuoka, A.; Komiya, S. J. Organomet. Chem. 1998, 569, 3
27. Zuo, W.-X.; Hua, R.; Qiu, X. Synth. Commun. 2004, 34, 3219
28. Nishiyama, Y.; Kakushou, F.; Sonoda, N. Tetrahedron Lett. 2005, 46, 787
29. Nishiyama, Y.; Shimoura, K.; Sonoda, N. Tetrahedron Lett. 2008, 49, 6533
30. Nishiyama, Y.; Kaiba, K.; Umeda, R. Tetrahedron Lett. 2010, 51, 793
31. Kuninobu, Y.; Ishii, E.; Takai, K. Angew. Chem., Int. Ed. 2007, 46, 3296
32. Kuninobu, Y.; Inoue, Y.; Takai, K. Chem. Lett. 2006, 35, 1376
33. Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319
34. Kuninobu, Y.; Ueda, H.; Takai, K. Chem. Lett. 2008, 37, 878
35. Bolm, C.; Kesselgruber, M.; Hermanns, N.; Hildebrand, J. P.; Raabe, G. Angew. Chem., Int. Ed. 2001, 40, 1488
36. Nakamura, M.; Endo, K.; Nakamura, E. J. Am. Chem. Soc. 2003, 125, 13002
37. Kuninobu, Y.; Kawata, A.; Takai, K. Org. Lett. 2005, 7, 4823
38. Kuninobu, Y.; Kawata, A.; Yudha, S. S.; Takata, H.; Nishi, M.; Takai, K. Pure Appl. Chem. 2010, 82, 1491
39. Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526
40. Ochida, A.; Ito, H.; Sawamura, M. J. Am. Chem. Soc. 2006, 128, 16486
41. Gao, Q.; Zheng, B.-F.; Li, J.-H.; Yang, D. Org. Lett. 2005, 7, 2185
42. Deng, C.-L.; Zou, T.; Wang, Z.-Q.; Song, R.-J.; Li, J.-H. J. Org. Chem. 2009, 74, 412
43. Deng, C.-L.; Song, R.-J.; Liu, Y.-L.; Li, J.-H. Adv. Synth. Catal. 2009, 351, 3096
44. Kuninobu, Y.; Yamashita, A.; Yamamoto, S.-i.; Yudha, S. S.; Takai, K. Synlett 2009, 3027
45. Zhao, W.-G.; Hua, R. Tetrahedron 2007, 63, 11803
46. Kusama, H.; Yamabe, H.; Onizawa, Y.; Hoshino, T.; Iwasawa, N. Angew. Chem., Int. Ed. 2005, 44, 468
47. Maeyama, K.; Iwasawa, N. J. Am. Chem. Soc. 1998, 120, 1928
48. Saito, K.; Onizawa, Y.; Kusama, H.; Iwasawa, N. Chem.-Eur. J. 2010, 16, 4716
49. Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104
50. Kusama, H.; Miyashita, Y.; Takaya, J.; Iwasawa, N. Org. Lett. 2006, 8, 289
51. Kuninobu, Y.; Yu, P.; Takai, K. Chem. Lett. 2007, 36, 1162
52. Yudha, S. S., Kuninobu, Y., and Takai, K. Angew. Chem., Int. Ed. 2008, 47, 9318
53. Kuninobu, Y.; Nishi, M.; Yudha, S. S.; Takai, K. Org. Lett. 2008, 10, 3009
54. Tsuji, H.; Yamagata, K.-i.; Fujimoto, T.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 7792
55. Yoshikai, N.; Zhang, S.; Yamagata, K.-i.; Tsuji, H.; Nakamura, E. J. Am. Chem. Soc. 2009, 131, 4099
56. Kuninobu, Y.; Iwanaga, T.; Nishi, M.; Takai, K. Chem. Lett. 2010, 39, 894
57. Kawata, A.; Kuninobu, Y.; Takai, K. Chem. Lett. 2009, 38, 836
58. Kondo, T.; Tsuji, Y.; Watanabe, Y. Tetrahedron Lett. 1988, 29, 3833
59. Hori, H.; Koike, K.; Takeuchi, K.; Ishitani, O. Chem. Lett. 2000, 29, 376
60. Farona, M. F.; Greenlee, W. S. J. Chem. Soc., Chem. Commun. 1975, 759
61. For examples, see
62. Ohmura, T.; Yorozuya, S.-i.; Yamamoto, Y.; Miyaura, N. Organometallics 2000, 19, 365
63. Rubina, M.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 11107
64. Ogoshi, S.; Ueta, M.; Oka, M.-a.; Kurosawa, H. Chem. Commun. 2004, 2732
65. Lee, C.-C.; Lin, Y.-C.; Liu, Y.-H.; Wang, Y. Organometallics 2005, 24, 136
66. Chen, X.; Xue, P.; Sung, H. H. Y.; Williams, I. D.; Peruzzini, M.; Bianchini, C.; Jia, G. Organometallics 2005, 24, 4330
67. Weng, W.; Guo, C.; Çelenligil-Çetin, R.; Foxman, B. M.; Ozerov, O. V. Chem. Commun. 2006, 197
68. Bustelo, E.; Dixneuf, P. H. Adv. Synth. Catal. 2007, 349, 933
69. Ogata, K.; Oka, O.; Toyota, A.; Suzuki, N.; Fukuzawa, S.-i. Synlett 2008, 2663
70. Kakiuchi, F.; Murai, S. Top. Organomet. Chem. 1999, 3, 47
71. Guari, Y.; Sabo-Etienne, S.; Chaudret, B. Eur. J. Inorg. Chem. 1999, 1047
72. Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698
73. Kakiuchi, F.; Kochi, T. Synthesis 2008, 3013
74. Waltz, K. M.; Hartwig, J. F. Science 1997, 277, 211
75. Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890
76. Kuninobu, Y.; Nishina, Y.; Okaguchi, K.; Shouho, M.; Takai, K. Bull. Chem. Soc. Jpn. 2008, 81, 1393
77. Kuninobu, Y.; Nishina, Y.; Shouho, M.; Takai, K. Angew. Chem., Int. Ed. 2006, 45, 2766
78. Kuninobu, Y.; Nishina, Y.; Takai, K. Org. Lett. 2006, 8, 2891
79. Kuninobu, Y.; Nishina, Y.; Kawata, A.; Shouho, M.; Takai, K. Pure Appl. Chem. 2008, 80, 1149
80. Kuninobu, Y.; Tokunaga, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2006, 128, 202
81. Kuninobu, Y.; Nishina, Y.; Nakagawa, C.; Takai, K. J. Am. Chem. Soc. 2006, 128, 12376
82. Kuninobu, Y.; Nishina, Y.; Takai, K. Tetrahedron 2007, 63, 8463
83. Kuninobu, Y.; Matsuki, T.; Takai, K. Org. Lett. 2010, 12, 2948
84. Kuninobu, Y.; Tokunaga, Y.; Takai, K. Chem. Lett. 2007, 36, 872
85. Kuninobu, Y.; Kikuchi, K.; Tokunaga, Y.; Nishina, Y.; Takai, K. Tetrahedron 2008, 64, 5974
86. Kuninobu, Y.; Fujii, Y.; Matsuki, T.; Nishina, Y.; Takai, K. Org. Lett. 2009, 11, 2711
87. Kuninobu, Y.; Nishina, Y.; Matsuki, T.; Takai, K. J. Am. Chem. Soc. 2008, 130, 14062
88. Kuninobu, Y.; Yu, P.; Takai, K. Org. Lett. 2010, 12, 4274
89. Zhang, Y. J.; Skucas, E.; Krische, M. J. Org. Lett. 2009, 11, 4248
90. Kuninobu, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2006, 128, 11368
91. Kuninobu, Y.; Morita, J.; Nishi, M.; Kawata, A.; Takai, K. Org. Lett. 2009, 11, 2535
92. Kuninobu, Y.; Kawata, A.; Nishi, M.; Yudha, S. S.; Chen, J.-j.; Takai, K. Chem. Asian J. 2009, 4, 1424
93. The promotion effect of isocyanide has also been reported by Suginome and Ito. See: Suginome, M.; Ito, Y.; Murai, S.) Top. Organomet. Chem. 1999, 3, 131.
94. Vitali, D.; Calderazzo, F. Gazz. Chim. Ital. 1972, 102, 587
95. Kuninobu, Y.; Kawata, A.; Nishi, M.; Takata, H.; Takai, K. Chem. Commun. 2008, 6360
96. Kuninobu, Y.; Takata, H.; Kawata, A.; Takai, K. Org. Lett. 2008, 10, 3133
97. Kuninobu, Y.; Nishi, M.; Kawata, A.; Takata, H.; Hanatani, Y.; Yudha, S. S.; Iwai, A.; Takai, K. J. Org. Chem. 2010, 75, 334
98. Yamamoto, K.; Hayashi, T. Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 2, pp 167-191.
99. Hayashi, T. Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 1, pp 319-333.
100. Yamamoto, K.; Hayashi, T. Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 2, pp 167-181.
101. Pedersen, H. L.; Johannsen, M. J. Org. Chem. 2002, 67, 7982
102. Glaser, P. B.; Tilley, T. D. J. Am. Chem. Soc. 2003, 125, 13640
103. Horino, Y.; Livinghouse, T. Organometallics 2004, 23, 12
104. Lewis, L. N.; Sy, K. G.; Bryant Jr, G. L.; Donahue, P. E. Organometallics 1991, 10, 3750
105. Takeuchi, R.; Yasue, H. Organometallics 1996, 15, 2098
106. Giraud, L.; Jenny, T. Organometallics 1998, 17, 4267
107. Chatani, N.; Kodama, T.; Kajikawa, Y.; Murakami, H.; Kakiuchi, F.; Ikeda, S.-i.; Murai, S. Chem. Lett. 2000, 29, 14
108. Yamamoto, Y.; Ohno, T.; Itoh, K. Organometallics 2003, 22, 2267
109. Itami, K.; Mitsudo, K.; Nishino, A.; Yoshida, J.-i. J. Org. Chem. 2002, 67, 2645
110. Sprengers, J. W.; De Greef, M.; Duin, M. A.; Elsevier, C. J. Eur. J. Inorg. Chem. 2003, 3811
111. Zhao, W.-G.; Hua, R. Eur. J. Org. Chem. 2006, 5495
112. Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675
113. Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104
114. Roesky, P. W.; Müller, T. E. Angew. Chem., Int. Ed. 2003, 42, 2708
115. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079
116. Müller, T. E.; Grosche, M.; Herdtweck, E.; Pleier, A.-K.; Walter, E.; Yan, Y. K. Organometallics 2000, 19, 170
117. Ouh, L. L.; Müller, T. E.; Yan, Y. K. J. Organomet. Chem. 2005, 690, 3774
118. Yudha, S. S.; Kuninobu, Y.; Takai, K. Org. Lett. 2007, 9, 5609
119. Liu, Y.; Hua, R.; Sun, H.-B.; Qiu, X. Organometallics 2005, 24, 2819
120. Hua, R.; Tian, X. J. Org. Chem. 2004, 69, 5782
121. Jiang, J.-L.; Hua, R. Tetrahedron Lett. 2006, 47, 953
122. Jiang, J.-L.; Gao, F.; Hua, R.; Qiu, Q. J. Org. Chem. 2005, 70, 381
123. Kawata, A.; Takata, K.; Kuninobu, Y.; Takai, K. Angew. Chem., Int. Ed. 2007, 46, 7793
124. Kuninobu, Y.; Kawata, A.; Noborio, T.; Yamamoto, S.-i.; Matsuki, T.; Takata, K.; Takai, K. Chem. Asian J. 2010, 5, 941
125. Davies, T. J.; Jones, R. V. H.; Lindsell, W. E.; Miln, C.; Preston, P. N. Tetrahedron Lett. 2002, 43, 487
126. Cooper, S. R. Acc. Chem. Res. 1988, 21, 141
127. Adams, R. D.; Falloon, S. B. J. Am. Chem. Soc. 1994, 116, 10540
128. Adams, R. D.; Falloon, S. B. Organometallics 1995, 14, 1748
129. Adams, R. D., Queisser, J. A., and Yamamoto, J. H. Organometallics 1996, 15, 2489
130. Adams, R. D.; Perrin, J. L.; Queisser, J. A.; Wolfe, J. B. Organometallics 1997, 16, 2612
131. Adams, R. D.; Huang, M.; Huang, W.; Queisser, J. A. J. Am. Chem. Soc. 1996, 118, 9442
132. Adams, R. D.; Huang, M.; Huang, W. Organometallics 1997, 16, 4479
133. Batchelor, R. J.; Einstein, F. W. B.; Gay, I. D.; Gu, J.-H.; Pinto, B. M.; Zhou, X.-M. J. Am. Chem. Soc. 1990, 112, 3706
134. Levason, W.; Quirk, J. J.; Reid, G. J. Chem. Soc., Dalton Trans. 1996, 3713
135. Hope, E. G.; Levason, W. Coord. Chem. Rev. 1993, 122, 109
136. Adams, R. D.; McBride, K. T. Chem. Commun. 1997, 525
137. Adams, R. D.; McBride, K. T. Organometallics 1997, 16, 3895
138. McAlees, A. J.; McCrindle, R. J. Chem. Soc., C 1969, 2425
139. He, D.-H., Wakasa, N., and Fuchikami, T. Tetrahedron Lett. 1995, 36, 1059
140. Sullivan, B. P.; Bolinger, C. M.; Conrad, D.; Vining, W. J.; Meyer, T. J. J. Chem. Soc., Chem. Commun. 1985, 1414
141. Hawecker, J.; Lehn, J.-M.; Ziessel, R. Helv. Chim. Acta 1986, 69, 1990
142. Hori, H.; Takano, Y.; Koike, K.; Sasaki, Y. Inorg. Chem. Commun. 2003, 6, 300
143. For a review, see
144. Takeda, H.; Ishitani, O. Coord. Chem. Rev. 2010, 254, 346
145. Ruiz, G.; Wolcan, E.; Capparelli, A. L.; Féliz, M. R. J. Photochem. Photobiol. A: Chem. 1995, 89, 61
146. Hori, H.; Johnson, F. P. A.; Koike, K.; Ishitani, O.; Ibusuki, T. J. Photochem. Photobiol., A 1996, 96, 171
147. Johnson, F. P. A.; George, M. W.; Hartl, F.; Turner, J. J. Organometallics 1996, 15, 3374
148. Hori, H.; Johnson, F. P. A.; Koike, K.; Takeuchi, K.; Ibusuki, T.; Ishitani, O. J. Chem. Soc., Dalton Trans. 1997, 1019
149. Koike, K.; Hori, H.; Ishizuka, M.; Westwell, J. R.; Takeuchi, K.; Ibusuki, T.; Enjouji, K.; Kanno, H.; Sakamoto, K.; Ishitani, O. Organometallics 1997, 16, 5724
150. Hori, H.; Ishihara, J.; Koike, K.; Takeuchi, K.; Ibusuki, T.; Ishitani, O. J. Photochem. Photobiol., A 1999, 120, 119
151. Hori, H.; Koike, K.; Takeuchi, K.; Sasaki, Y. Chem. Lett. 2000, 522
152. Sung-Suh, H. M.; Kim, D. S.; Lee, C. W.; Park, S.-E. Appl. Organomet. Chem. 2000, 14, 826
153. Hwang, J.-S.; Kim, D. S.; Lee, C. W.; Park, S.-E. Korean J. Chem. Eng. 2001, 18, 919
154. Hayashi, Y.; Kita, S.; Brunschwig, B. S.; Fujita, E. J. Am. Chem. Soc. 2003, 125, 11976
155. Kurz, P.; Probst, B.; Spingler, B.; Alberto, R. Eur. J. Inorg. Chem. 2006, 2966
156. Takeda, H.; Koike, K.; Inoue, H.; Ishitani, O. J. Am. Chem. Soc. 2008, 130, 2023
157. Abu-Abdoun, I. I. Polym. Int. 1999, 48, 1197
158. Abu-Abdoun, I. I. Des. Monomers Polym. 2000, 3, 171
159. Arceo, E.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2010, 132, 11408