Browse > Article
http://dx.doi.org/10.5012/bkcs.2007.28.12.2139

Ruthenium Complex-catalyzed Highly Selective Co-oligomerization of Alkenes  

Ura, Yasuyuki (Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University)
Tsujita, Hiroshi (Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University)
Mitsudo, Take-Aki (Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University)
Kondo, Teruyuki (Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University)
Publication Information
Abstract
Ruthenium complex-catalyzed reactions often require highly qualified tuning of reaction conditions with substrates to attain high yield and selectivity of the products. In this review, our strategies for achieving characteristic ruthenium complex-catalyzed co-oligomerization of different alkenes are disclosed: 1) The codimerization of 2-norbornenes with acrylic compounds by new ruthenium catalyst systems of RuCl3(tpy)/Zn [tpy = 2,2':6',2''-terpyridine] or [RuCl2(η6-C6H6)]2/Zn in alcohols, 2) A novel synthesis of 2-alkylidenetetrahydrofurans from dihydrofurans and acrylates by zerovalent ruthenium catalysts, such as Ru(η4-cod)(η6-cot) [cod = 1,5-cyclooctadiene, cot = 1,3,5-cyclooctatriene] and Ru(η6-cot)(η2-dmfm)2 [dmfm = dimethyl fumarate], 3) Regio- and stereoselective synthesis of enamides by Ru(η6-cot)(η2-dmfm)2-catalyzed codimerization of N-vinylamides with alkenes, and 4) Unusual head-to-head dimerization of styrenes and linear codimerization of styrenes with ethylene by Ru(η6-cot)(η2-dmfm)2 catalyst in the presence of primary alcohols.
Keywords
Ruthenium; Catalyst; Co-oligomerization; Alkenes; Atom-efficiency;
Citations & Related Records

Times Cited By Web Of Science : 10  (Related Records In Web of Science)
Times Cited By SCOPUS : 10
연도 인용수 순위
1 Mitsudo, T.; Suzuki, T.; Zhang, S.-W.; Imai, D.; Fujita, K.; Manabe, T.; Shiotsuki, M.; Watanabe, Y.; Wada, K.; Kondo, T. J. Am. Chem. Soc. 1999, 121, 1839
2 Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 24, 679   DOI
3 Trost, B. M.; Imi, K.; Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371   DOI   ScienceOn
4 Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 66, 529
5 Sato, T.; Kakiuchi, F.; Chatani, N.; Murai, S. Chem. Lett. 1998, 27, 893   DOI
6 Lim, Y.-G.; Kang, J.-B.; Kim, Y. H. J. Chem. Soc., Chem. Comum. 1996, 585
7 Ruthenium in Organic Synthesis; Murahashi, S.-I., Ed.; Wiley- VCH: Weinheim, 2004
8 Mitsudo, T.; Ura, Y.; Kondo, T. Chem. Rec. 2006, 6, 107   DOI   ScienceOn
9 Hahn, C.; Cucciolito, M. E.; Vitagliano, A. J. Am. Chem. Soc. 2002, 124, 9038   DOI   ScienceOn
10 Mitsudo, T.; Kokuryo, K.; Takegami, Y. J. Chem. Soc., Chem. Commun. 1976, 772
11 Mitsudo, T.; Kokuryo, K.; Shinsugi, T.; Nakagawa, Y.; Watanabe, Y.; Takegami, Y. J. Org. Chem. 1979, 44, 4492   DOI
12 Mitsudo, T.; Hori, Y.; Watanabe, Y. J. Organomet. Chem. 1987, 334, 157   DOI   ScienceOn
13 Shell Dev. Co. US Patent, 3.635.937, 3.637.636, 3.644.536, 3.644.564, 3.647.914, 3.647.915, 3.661.803, 3.686.159, 1972
14 Crabtree, R. H. The Organometallic Chemistry of the Transition Metals, 4th Ed.; John Wiley & Sons, Inc.: New Jersey, 2005
15 Mitsudo, T.; Zhang, S.-W.; Nagao, M.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1991, 598
16 Yi, C. S.; He, Z.; Lee, D. W. Organometallics 2001, 20, 802   DOI   ScienceOn
17 Bogdanovic, B.; Henc, B.; Loser, A.; Meister, B.; Pauling, H.; Wilke, G. Angew. Chem. Int. Ed. 1973, 12, 954   DOI
18 Muller, G.; Ordinas, J. I. J. Mol. Catal. A: Chemical 1997, 125, 97   DOI   ScienceOn
19 Marciniec, B.; Kownacki, I.; Kubicki, M. Organometallics 2001, 20, 3423   DOI   ScienceOn
20 Kretschmer, W. P.; Troyanov, S. I.; Meetsma, A.; Hassen, B.; Teuben, J. H. Organometallics 1998, 17, 284   DOI   ScienceOn
21 Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 2002, 124, 734   DOI   ScienceOn
22 RajanBabu, T. V. Chem. Rev. 2003, 103, 2845 and references therein   DOI   ScienceOn
23 Bedford, R. B.; Betham, M.; Blake, M. E.; Garces, A.; Millar, S. L.; Prashar, S. Tetrahedron 2005, 61, 9799   DOI   ScienceOn
24 Grutters, M. M. P.; Müller, C.; Vogt, D. J. Am. Chem. Soc. 2006, 128, 7414   DOI   ScienceOn
25 Jackson, W. P.; Ley, S. V.; Morton, J. A. Tetrahedron Lett. 1981, 22, 2601   DOI   ScienceOn
26 Jackson, W. P.; Ley, S. V.; Whittle, A. J. J. Chem. Soc., Chem. Commun. 1980, 1173
27 Marciniec, B.; Kownacki, I.; Kubicki, M. Organometallics 2002, 21, 3263   DOI   ScienceOn
28 Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067   DOI   ScienceOn
29 Ura, Y.; Tsujita, H.; Wada, K.; Kondo, T.; Mitsudo, T. J. Org. Chem. 2005, 70, 6623   DOI   ScienceOn
30 Faissner, R.; Huttner, G. Eur. J. Inorg. Chem. 2003, 2239
31 Ito, T.; Kawai, T.; Takami, Y. Tetrahedron Lett. 1972, 13, 4775   DOI   ScienceOn
32 Saegusa, T.; Ito, Y.; Tomita, S.; Kinoshita, H. J. Org. Chem. 1970, 35, 670   DOI
33 Barlow, M. G.; Bryant, M. J.; Haszeldine, R. N.; Mackie, A. G. J. Organomet. Chem. 1970, 21, 215   DOI   ScienceOn
34 Mitsudo, T.; Zhang, S.-W.; Kondo, T.; Watanabe, Y. Tetrahedron Lett. 1992, 33, 341
35 Kawakami, K.; Kawata, N.; Maruya, K.; Mizoroki, T.; Ozaki, A. J. Catal. 1975, 39, 134   DOI   ScienceOn
36 McKinney, R. J. Organometallics 1986, 5, 1752   DOI
37 Mitsudo, T.; Naruse, H.; Kondo, T.; Ozaki, Y.; Watanabe, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 580   DOI   ScienceOn
38 Mitsudo, T.; Nakagawa, Y.; Watanabe, K.; Hori, Y.; Misawa, H.; Watanabe, H.; Watanabe, Y. J. Org. Chem. 1985, 50, 565   DOI
39 Nikishin, G. I.; Klimova, T. E.; Ignatenko, A. V.; Kovalev, I. P. Tetrahedron Lett. 1991, 32, 1077   DOI   ScienceOn
40 Mitsudo, T.; Nakagawa, Y.; Watanabe, H.; Watanabe, K.; Misawa, H.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1981, 496
41 El Amrani, M. A.; Mortreux, A.; Petit, F. Tetrahedron Lett. 1989, 30, 6515   DOI   ScienceOn
42 Cros, P.; Triantaphylides, C.; Buono, G. J. Org. Chem. 1988, 53, 185   DOI
43 Oehme, G.; Grassert, I.; Mennenga, H.; Baudisch, H. J. Mol. Catal. 1986, 37, 53   DOI   ScienceOn
44 Hilt, G.; du Mesnil, F.; Luers, S. Angew. Chem. Int. Ed. 2001, 40, 387   DOI   ScienceOn
45 Fujiwara, M.; Nishikawa, T.; Hori, Y. Org. Lett. 1999, 1, 1635   DOI   ScienceOn
46 Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 24, 679   DOI
47 Masuda, K.; Ohkita, H.; Kurumatani, S.; Itoh, K. J. Organomet. Chem. 1993, 454, C13   DOI   ScienceOn
48 Kumareswaran, R.; Nandi, M.; RajanBabu, T. V. Org. Lett. 2003, 5, 4345   DOI   ScienceOn
49 Mitsudo, T.; Ura, Y.; Kondo, T. J. Organomet. Chem. 2004, 689, 4530   DOI   ScienceOn
50 Mitsudo, T.; Kondo, T. Synlett 2001, 309
51 Bryson, T. A. J. Org. Chem. 1973, 38, 3428. 39   DOI
52 Trost, B. M.; Frederiksen, M. U.; Rudd, M. T. Angew. Chem. Int. Ed. 2005, 44, 6630   DOI   ScienceOn
53 Nakada, M.; Iwata, Y.; Takano, M. Tetrahedron Lett. 1999, 40, 9077   DOI   ScienceOn
54 Yamaguchi, M.; Hirao, I. Chem. Lett. 1985, 14, 337   DOI
55 Pound, M. K.; Davies, D. L.; Pilkington, M.; de Pina Vaz Sousa, M. M.; Wallis, J. D. Tetrahedron Lett. 2002, 43, 1915   DOI   ScienceOn
56 Schmid, H.; Naab, P.; Hayakawa, K. Helv. Chim. Acta 1978, 61, 1427   DOI
57 Huang, X.; Zhu, J.; Lin, Z. Organometallics 2004, 23, 4154   DOI   ScienceOn
58 Brookhart, M.; Hauptman, E. J. Am. Chem. Soc. 1992, 114, 4437   DOI
59 Hauptman, E.; Sabo-Etienne, S.; White, P. S.; Brookhart, M.; Garner, J. M.; Fagan, P. J.; Calabrese, J. C. J. Am. Chem. Soc. 1994, 116, 8038
60 Kawamoto, K.; Tatani, A.; Imanaka, T.; Teranishi, S. Bull. Chem. Soc. Jpn. 1971, 44, 1239   DOI
61 Bochmann, M.; Thomas, M. J. Mol. Catal. 1984, 26, 79   DOI   ScienceOn
62 Grenouillet, P.; Neibecker, D.; Tkatchenko, I. J. Chem. Soc., Chem. Commun. 1983, 542
63 Ito, T.; Takami, Y. Bull. Chem. Soc. Jpn. 1978, 51, 1220   DOI
64 Langer, P.; Bellur, E. J. Org. Chem. 2003, 68, 9742   DOI   ScienceOn
65 Ito, T.; Takahashi, K.; Takami, Y. Tetrahedron Lett. 1973, 14, 5049   DOI   ScienceOn
66 Lygo, B.; O'Connor, N. Tetrahedron Lett. 1987, 28, 3597   DOI   ScienceOn
67 Batra, S.; Srivastava, S.; Singh, K.; Chander, R.; Khanna, A. K.; Bhaduri, A. P. Bioorg. Med. Chem. 2000, 8, 2195   DOI   ScienceOn
68 Kato, K.; Sasaki, T.; Takayama, H.; Akita, H. Tetrahedron 2003, 59, 2679   DOI   ScienceOn
69 Kato, K.; Nishimura, A.; Yamamoto, Y.; Akita, H. Tetrahedron Lett. 2001, 42, 4203   DOI   ScienceOn
70 Kato, K.; Tanaka, M.; Yamamura, S.; Yamamoto, Y.; Akita, H. Tetrahedron Lett. 2003, 44, 3089   DOI   ScienceOn
71 Langer, P.; Holtz, E.; Karime, I.; Saleh, N. N. R. J. Org. Chem. 2001, 66, 6057   DOI   ScienceOn
72 Langer, P.; Krummel, T. Chem. Eur. J. 2001, 7, 1720   DOI   ScienceOn
73 Langer, P.; Freifeld, I. Chem. Eur. J. 2001, 7, 565   DOI   ScienceOn
74 Mitsudo, T.; Ura, Y.; Kondo, T.; Wada, K.; Tsujita, H.; Matsuki, S. (Kyoto University), WO 2007026654, 2007
75 Langer, P.; Eckardt, T. Angew. Chem. Int. Ed. 2000, 39, 4343   DOI   ScienceOn
76 Langer, P.; Holtz, E. Angew. Chem. Int. Ed. 2000, 39, 3086   DOI   ScienceOn
77 Wakatsuki, Y.; Yamazaki, H. J. Organomet. Chem. 1995, 500, 349   DOI   ScienceOn
78 Jiang, Z.; Sen, A. J. Am. Chem. Soc. 1990, 112, 9655   DOI
79 Jiang, Z.; Sen, A. Organometallics 1993, 12, 1406   DOI   ScienceOn
80 Tsuchimoto, T.; Kamiyama, S.; Negoro, R.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2003, 852
81 DiRenzo, G. M.; White, P. S.; Brookhart, M. J. Am. Chem. Soc. 1996, 118, 6225   DOI   ScienceOn
82 Tsujita, H.; Ura, Y.; Wada, K.; Kondo, T.; Mitsudo, T. Chem. Commun. 2005, 5100
83 Lygo, B. Tetrahedron 1988, 44, 6889   DOI   ScienceOn
84 Barrett, A. G. M.; Sheth, H. G. J. Org. Chem. 1983, 48, 5017   DOI
85 Lee, J. Y.; Kim, B. H. Tetrahedron Lett. 1995, 36, 3361   DOI   ScienceOn
86 Takano, S.; Tomita, S.; Takahashi, M.; Ogasawara, K. Synthesis 1987, 1116
87 Furstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863   DOI   ScienceOn
88 Nelson, J. E.; Bercaw, J. E.; Labinger, J. A. Organometallics 1989, 8, 2484   DOI
89 Solladie, G.; Dominguez, C. J. Org. Chem. 1994, 59, 3898   DOI   ScienceOn
90 Kim, B. H.; Lee, J. Y. Tetrahedron Lett. 1993, 34, 1609   DOI   ScienceOn
91 Burger, B. J.; Santarsiero, B. D.; Trimmer, M. S.; Bercaw, J. E. J. Am. Chem. Soc. 1988, 110, 3134   DOI
92 Milet, A.; Dedieu, A.; Kapteijn, G.; van Koten, G. Inorg. Chem. 1997, 36, 3223   DOI   ScienceOn
93 Higashimura, M.; Imamura, K.; Yokogawa, Y.; Sakakibara, T. Chem. Lett. 2004, 33, 728   DOI   ScienceOn
94 Hajra, S.; Maji, B.; Karmakar, A. Tetrahedron Lett. 2005, 46, 8599   DOI   ScienceOn
95 Piotti, M. E.; Alper, H. J. Org. Chem. 1997, 62, 8484   DOI   ScienceOn
96 Gabriele, B.; Salerno, G.; Pascali, F. D.; Costa, M.; Chiusoli, G. P. J. Organomet. Chem. 2000, 593-594, 409
97 Cacchi, S.; Fabrizi, G.; Moro, L. J. Org. Chem. 1997, 62, 5327   DOI   ScienceOn
98 Koch, G.; Pfaltz, A. Tetrahedron: Asymmetry 1996, 7, 2213   DOI   ScienceOn
99 Tsuji, J. Pure Appl. Chem. 1982, 54, 197   DOI
100 Furstner, A.; Szillat, H.; Stelzer, F. J. Am. Chem. Soc. 2000, 122, 6785   DOI   ScienceOn
101 Casty, G. L.; Stryker, J. M. Organometallics 1997, 16, 3083   DOI   ScienceOn
102 Dunkerton, L. V.; Serino, A. J. J. Org. Chem. 1982, 47, 2812   DOI
103 Sui-Seng, C.; Groux, L. F.; Zargarian, D. Organometallics 2006, 25, 571   DOI   ScienceOn
104 Sui-Seng, C.; Castonguay, A.; Chen, Y.; Gareau, D.; Groux, L. F.; Zargarian, D. Top. Catal. 2006, 37, 81   DOI   ScienceOn
105 Barthelemy, P.; Deffieux, A.; Sigwalt, P. Nouv. J. Chem. 1985, 173
106 Dawans, F. Tetrahedron Lett. 1971, 22, 1943
107 Grenouillet, P.; Neibecker, D.; Tkatchenko, I. Organometallics 1984, 3, 1130   DOI
108 Kaneda, K.; Kiriyama, T.; Hiraoka, T.; Imanaka, T. J. Mol. Catal. 1988, 48, 343   DOI   ScienceOn
109 Grenoulllet, P.; Neibecker, D.; Tkatchenko, I. Organometallics 1984, 3, 1130   DOI
110 Ura, Y.; Utsumi, T.; Tsujita, H.; Wada, K.; Kondo, T.; Mitsudo, T. Organometallics 2006, 25, 2934   DOI   ScienceOn
111 Shiotsuki, M.; Suzuki, T.; Wada, K.; Kondo, T.; Mitsudo, T. Organometallics 2000, 19, 5733   DOI   ScienceOn
112 Kawamoto, K.; Tatani, A.; Imanaka, T.; Teranishi, S. Bull. Chem. Soc. Jpn. 1971, 44, 1239   DOI
113 Kondo, T.; Takagi, D.; Tsujita, H.; Ura, Y.; Wada, K.; Mitsudo, T. Angew. Chem. Int. Ed. 2007, in press
114 Sen, A.; La1, T.-W. Organometallics 1983, 2, 1059
115 Barlow, M. G.; Bryant, M. J.; Haszeldine, R. N.; Mackie, A. G. J. Organomet. Chem. 1970, 21, 215   DOI   ScienceOn
116 Ferraz, H. M. C.; Sano, M. K.; Nunes, M. R. S.; Bianco, G. G. J. Org. Chem. 2002, 67, 4122   DOI   ScienceOn
117 Krueger, S. A.; Bryson, T. A. J. Org. Chem. 1974, 39, 3167   DOI
118 Han, X.; Wang, X.; Pei, T.; Widenhoefer, R. A. Chem. Eur. J. 2004, 10, 6333   DOI   ScienceOn
119 Yang, D.; Li, J.-H.; Gao, Q.; Yan, Y.-L. Org. Lett. 2003, 5, 2869   DOI   ScienceOn
120 Kramer, B.; Averhoff, A.; Waldvogel, S. R. Angew. Chem. Int. Ed. 2002, 41, 2981   DOI   ScienceOn
121 Kondo, T.; Tsunawaki, F.; Ura, Y.; Sadaoka, K.; Iwasa, T.; Wada, K.; Mitsudo, T. Organometallics 2005, 24, 905   DOI   ScienceOn
122 Longo, P.; Proto, A.; Zambelli, A. Macromol. Chem. Phys. 1995, 196, 3015   DOI   ScienceOn
123 Henrici- Olive, G.; Olive, S.; Schmidt, E. J. Organomet. Chem. 1972, 39, 201
124 Lapointe, A. M.; Rix, F. C.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 906   DOI   ScienceOn
125 Zambelli, A.; Pellecchia, C.; Proto, A. Macromol. Symp. 1995, 89, 373   DOI   ScienceOn
126 Bedford, R. B.; Betham, M.; Blake, M. E.; Garce's, A.; Millar, S. L.; Prashar, S. Tetrahedron 2005, 61, 9799   DOI   ScienceOn
127 Peng, J.; Li, J.; Qiu, H.; Jiang, J.; Jiang, K.; Mao, J.; Lai, G. J. Mol. Catal. A: Chemical 2006, 255, 16   DOI   ScienceOn
128 Mitsudo, T.; Hori, Y.; Watanabe, Y. Bull. Chem. Soc. Jpn. 1986, 59, 3201   DOI
129 Ruthenium Catalysts and Fine Chemistry; Bruneau, C., Dixneuf, P. H., Eds.; Springer-Verlag: Berlin, 2004
130 Brookhart, M.; Sabo-Etienne, S. J. Am. Chem. Soc. 1991, 113, 2777
131 Bartlett, P. A.; Meadows, J. D.; Ottow, E. J. Am. Chem. Soc. 1984, 106, 5304   DOI
132 Galdi, N.; Monica, C. D.; Spinella, A.; Oliva, L. J. Mol. Catal. A: Chemical 2006, 243, 106   DOI   ScienceOn
133 Tsujita, H.; Ura, Y.; Matsuki, S.; Wada, K.; Mitsudo, T.; Kondo, T. Angew. Chem. Int. Ed. 2007, 46, 5160   DOI   ScienceOn
134 Yet, L. Chem. Rev. 2003, 103, 4283   DOI   ScienceOn
135 Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc. Chem. Commun. 1995, 413
136 Bosmann, A.; Franciò, G.; Janssen, E.; Solinas, M.; Leitner, W.; Wasserscheid, P. Angew. Chem. Int. Ed. 2001, 40, 2697   DOI   ScienceOn
137 Kawata, N.; Maruya, K.; Mizoroki, T.; Ozaki, A. Bull. Chem. Soc. Jpn. 1974, 47, 413   DOI
138 Shen, R.; Lin, C.; Bowman, T. E. J.; Bowman, Jr. B. J.; Porco, J. A. J. Am. Chem. Soc. 2003, 125, 7889   DOI   ScienceOn
139 Dehli, J. R.; Legros, J.; Bolm, C. Chem. Commun. 2005, 973, and references therein
140 Catellani, M.; Chiusoli, G. P.; Costa, M. J. Organomet. Chem. 1995, 500, 69   DOI   ScienceOn
141 GooBen, L. J.; Rauhaus, J. E.; Deng, G. Angew. Chem. Int. Ed. 2005, 44, 4042   DOI   ScienceOn
142 Hosokawa, T.; Takano, M.; Kuroki, Y.; Murahashi, S.-I. Tetrahedron Lett. 1992, 33, 6643
143 Yang, D.; Gao, Q.; Lee, C.-S.; Cheung, K.-K. Org. Lett. 2002, 4, 3271
144 Kato, K.; Yamamoto, Y.; Akita, H. Tetrahedron Lett. 2002, 43, 4915   DOI   ScienceOn
145 Timokhin, V. I.; Stahl, S. S. J. Am. Chem. Soc. 2005, 127, 17888   DOI   ScienceOn
146 Ninomiya, I.; Tada, Y.; Kiguchi, T.; Yamamoto, O.; Naito, T. J. Chem. Soc. Perkin Trans. 1 1984, 2035   DOI
147 Yi, C. S.; He, Z.; Lee, D. W. Organometallics 2001, 20, 802   DOI   ScienceOn
148 Lee, J. M.; Ahn, D.-S.; Jung, D. Y.; Lee, J.; Do, Y.; Kim, S. K.; Chang, S. J. Am. Chem. Soc. 2006, 128, 12954   DOI   ScienceOn
149 Stille, J. K.; Becker, Y. J. Org. Chem. 1980, 45, 2139   DOI
150 Krompiec, S.; Pigulla, M.; Krompiec, M.; Baj, S.; Mrowiec- , J.; Kasperczyk, J. Tetrahedron Lett. 2004, 45, 5257, and references therein   DOI   ScienceOn
151 Ninomiya, I.; Hashimoto, C.; Kiguchi, T.; Naito, T. J. Chem. Soc. Perkin Trans. 1 1984, 2911   DOI
152 Lesniak, S.; Pasternak, B. Synth. Commun. 2002, 32, 875   DOI   ScienceOn
153 Ziegler, K.; Gellert, H.; Kuhlhorn, H.; Martin, H.; Meyer, K.; Nagel, K.; Sauer, H.; Zoser, K. Angew. Chem. 1952, 64, 323   DOI
154 Langer, P.; Armbrust, H.; Eckardt, T.; Magull, J. Chem. Eur. J. 2002, 8, 1443   DOI   ScienceOn
155 Scheffler, J.-L.; Bette, V.; Mortreux, A.; Nowogrocki, G.; Carpentier, J.-F. Tetrahedron Lett. 2002, 43, 2679
156 Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis, 2nd ed.; Wiley-VCH: Weinheim, 2002
157 Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 2004; Vols 1-2
158 Trost, B. M. Acc. Chem. Res. 2002, 35, 695   DOI   ScienceOn
159 Applied Homogeneous Catalysis with Organometallic Compounds, 2nd Ed.; Colins, B.; Herrmann, W. A., Eds.; Wiley-VCH: New York, 2002; Vols. 1-3
160 Ziegler, K. Angew. Chem. 1964, 76, 545   DOI
161 Industrial Organic Chemistry, 3rd ed.; Weissermel, K., Arpe, H.- J., Eds.; Wiley-VCH: Weinheim, 2004
162 Kondo, T.; Mitsudo, T. Chem. Lett. 2005, 34, 893
163 Nandi, M.; Jin, J.; RajanBabu, T. V. J. Am. Chem. Soc. 1999, 121, 9899   DOI   ScienceOn
164 RajanBabu, T. V.; Nomura, N.; Jin, J.; Radetich, B.; Park, H.; Nandi, M. Chem. Eur. J. 1999, 5, 1963   DOI
165 Jin, J.; RajanBabu, T. V. Tetrahedron 2000, 56, 2145   DOI   ScienceOn
166 Bogdanoviae, B. Adv. Organomet. Chem. 1979, 17, 105   DOI
167 Kabalka, G. W.; Dong, G.; Venkataiah, B. Tetrahedron Lett. 2004, 45, 2775   DOI   ScienceOn
168 Leonard, J.; Mohialdin, S.; Reed, D.; Ryan, G.; Jones, M. F. J. Chem. Soc., Chem. Commun. 1993, 23
169 Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187   DOI   ScienceOn
170 Wu, G.; Rheingold, L. A.; Heck, R. F. Organometallics 1987, 6, 2386   DOI
171 Yamamoto, Y.; Nakagai, Y.; Ohkoshi, N.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6372. For a review, see: ref. 28a, pp 95-128
172 Nomura, N.; Jin, J.; Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 459   DOI   ScienceOn
173 Ceder, R.; Muller, G.; Ordinas, J. I. J. Mol. Catal. 1994, 92, 127   DOI   ScienceOn
174 Monteiro, A. L.; Seferin, M.; Dupont, J.; de Souza, R. F. Tetrahedron Lett. 1996, 37, 1157   DOI   ScienceOn
175 Fassina, V.; Ramminger, C.; Seferin, M.; Monteiro, A. L. Tetrahedron 2000, 56, 7403   DOI   ScienceOn
176 Bayersdorfer, R.; Ganter, B.; Englert, U.; Keim, W.; Vogt, D. J. Organomet. Chem. 1998, 552, 187   DOI   ScienceOn
177 Hovestad, N. J.; Eggeling, E. B.; Heidbüchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem. Int. Ed. 1999, 38, 1655   DOI
178 Eggeling, E. B.; Hovestad, N. J.; Jastrzebski, J. T. B. H.; Vogt, D.; van Koten, G. J. Org. Chem. 2000, 65, 8857   DOI   ScienceOn
179 Pillai, S. M.; Tembe, G. L.; Ravindranathan, M. J. Mol. Catal. 1993, 84, 77   DOI   ScienceOn
180 Umezaki, H.; Fujiwara, Y.; Sawara, K.; Teranishi, S. Bull. Chem. Soc. Jpn. 1973, 46, 2230   DOI
181 Wilke, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 185, and references therein
182 Britovsek, G. J. P.; Cavell, K. J.; Keim, W. J. Mol. Catal. A: Chemical 1996, 110, 77   DOI   ScienceOn
183 Solladie, G.; Salom-Roig, X. J.; Hanquet, G. Tetrahedron Lett. 2000, 41, 2737
184 Hoye, T. R.; Crawford, K. B. J. Org. Chem. 1994, 59, 520   DOI   ScienceOn
185 Nicola, T.; Vieser, R.; Eberbach, W. Eur. J. Org. Chem. 2000, 527
186 Trost, B. M.; Runge, T. A. J. Am. Chem. Soc. 1981, 103, 7550   DOI
187 Batmangherlich, S.; Davidson, A. H. J. Chem. Soc., Chem. Commun. 1985, 1399
188 Danishefsky, S.; Etheredge, S. J.; Dynak, J.; McCurry, P. J. Org. Chem. 1974, 39, 2658   DOI
189 Solladie, G.; Salom-Roig, X. J.; Hanquet, G. Tetrahedron Lett. 2000, 41, 551
190 Alderson, T.; Jenner, E. L.; Lindsey, Jr., R. V. J. Am. Chem. Soc. 1965, 87, 5638   DOI
191 Britovsek, G. J. P.; Keim, W.; Mecking, S.; Sainz, D.; Wagner, T. J. Chem. Soc., Chem. Commun. 1993, 1632
192 Tang, E.; Huang, X.; Xu, W.-M. Tetrahedron 2004, 60, 9963   DOI   ScienceOn
193 Ohta, S.; Shimabayashi, A.; Hayakawa, S.; Sumino, M.; Okamoto, M. Synthesis 1985, 45
194 Tiecco, M.; Testaferri, L.; Tingoli, M.; Bartoli, D.; Balducci, R. J. Org. Chem. 1990, 55, 429   DOI
195 Brussani, G.; Ley, S. V.; Wright, J. L.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1 1986, 303   DOI
196 Jackson, W. P.; Ley, S. V.; Morton, J. A. J. Chem. Soc., Chem. Commun. 1980, 1028