Aqueous Barbier-Type Reaction Mediated by Various Metals

Abstract

By the virtue of green chemistry, high efficiency, operational simplicity and mechanism stratagem, the aqueous Barbier-Type reactions have attracted chemists’ attention deeply in these recent twenty years. Numbers of metals were developed to catalyze these environmentally friendly reactions. However, these catalyzers often show different catalytic capability in their pre-requisite conditions, and provide different chem-, regio- and stereo-slectivities. Here, we try to summarize all these excellent results and give a comprehensive introduction.

Key words: aqueous media, Barbier-type, green chemistry, metal-mediated

Cite this article

TAN Xiang-Hui, ZHAO Hui, HOU Yong-Quan, LIU Lei, GUO Qing-Xiang. Aqueous Barbier-Type Reaction Mediated by Various Metals[J]. Chinese Journal of Organic Chemistry, 2004, 24(9): 987-1003.

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1 (a) Li, C. J. Chem. Rev. 1993,93, 2023.
(b) Sammelson, R. E.; Kurth, M. J. Chem. Rev. 2001, 101, 137.
(c) Siskin, M.; Katritzky, A. R. Chem. Rev. 2001, 101, 4.
2 Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017.
3 Haberman, J. X.; Irvin, G. C.; John, V. T.; Li, C. J. Green Chem. 1999, 265.
4 (a) Ranu, B. C.; Samanta, S.; Hajra, A. J. Org. Chem. 2001, 66, 7519.
(b) Lombardo, M.; Girotti, R.; Morganti, S.; Trombini, C. Org. Lett.2001, 3, 2981.
5 (a) Chan, T. H.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181.
(b) Chan, T. H.; Lee, M. C. J. Org. Chem. 1995,36, 517.
6 Choudhury, P. K.; Foubelo, F.; Yus, M. Tetrahedron Lett. 1998, 39, 3581.
7 Nair, V.; Jayan, C. N. Tetrahedron Lett. 2000, 41, 1091.
8 Li, C. J. Tetrahedron Lett. 1995, 36, 517.
9 Chen, D. L.; Li, C. J. Tetrahedron Lett. 1996, 37, 295.
10 Kwon, J. S.; Pae, A. N.; Choi, K. I.; Koh, H. Y.; Kim, Y.; Cho,Y. S. Tetrahedron Lett. 2001, 42, 1957.
11 Yadav, J. S.; Reddy, B. V.; Kiran, G. S. Tetrahedron Lett.2000, 41, 2695.
12 (a) Bernardi, L.; Cere, W.; Femoni, C.; Pollicino, S.; Ricci, A. J. Org. Chem. 2003, 68, 3348.
(b) Chan, T. H.; Lu, W. Tetrahedron Lett. 1998, 39, 8605.
(c) Kumar, H. M. S.; Anjaneyulu, S.; Reddy, S. J.; Yadav, S. Tetrahedron Lett. 2000, 41, 9311.
(d) Vilaivan, T.; Winopatan, C.; Shinada, T.; Ohfune, Y. Tetrahedron Lett. 2001, 42, 9073.
13 Lu, W.; Chan, T. H. J. Org. Chem. 2000, 65, 8589.
14 Loh, T. P.; Lye, P. L.; Wang, R. B.; Sim, K. Y. Tetrahedron Lett. 2000, 41, 7779.
15 (a) Auge, J.; Lubin-Germain, N.; Seghrouchni, L. TetrahedronLett. 2002, 43, 5255.
(b) Auge, J.; Lubin-Germain, N.; Seghrouchni, L. Tetrahedron Lett.2003, 44, 819.
(c) Chappell, M. D.; Halcomb, R. L. Org. Lett. 2000, 2, 2003.
(d) Loh, T. P.; Li, X. R. Tetrahedron Lett. 1997, 38, 369.
(e) Li, C. J.; Chen, D. L.; Lu, Y. Q.; Hamberman, J. X.; Mague, J. T. Tetrahedron 1998, 54, 2347.
(f) Yoo, J.; Oh, K. E.; Keum, G.; Kang, S. B.; Kim, Y. Polyhedron 2000, 19, 549.
(g) Shin, J. A.; Choi, K. I.; Pae, A. N.; Koh, H. Y.; Kang, H. Y.; Cho,Y. S. J. Chen. Soc., Perkin Trans. 1. 2001, 946.
16 (a) Lu, W. S.; Ma, J.; Yang, Y.; Chan, T. K. Org. Lett. 2000, 2, 3469.
(b) Chan, T. K.; Lu, W. S. Tetrahedron Lett. 1998, 39, 8605.
17 Araki, S.; Jin, S. J.; Idou, Y.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1992, 65, 1736.
18 (a) Auge, J.; Germain, N. L.; Woaye, A. T. Tetrahedron Lett. 1999, 40, 9245.
(b) Hilt, G.; Smolko, K. I.; Waloch, C. Tetrahedron Lett. 2002, 43, 1437.
19 Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry 1996, 7, 1535.
20 Viswanathan, G. S.; Yang, J.; Li, C. J. Org. Lett. 1999, 1, 993.
21 Onishi, Y.; Ogawa, D.; Yasuda, M.; Baba, A. J. Am. Chem. Soc. 2002, 124, 13691.
22 Killinger, T. A.; Boughton, N. A.; Runge, T. A.; Wolinsky, J.J. Organomet. Chem. 1977, 124, 131.
23 (a)Einhorn, C.; Luche, J. L. J. Organomet. Chem. 1987, 322, 177.
(b) Petrier, C.; Einhorn, J.; Luche, J. L. Tetrahedron 1985, 11, 1449.
24 Wilson, S. R.; Guazzaroni, M. E. J. Org. Chem. 1989, 54, 3087.
25 (a) Mattes, H.; Benezra, C. Tetrahedron Lett. 1985, 26, 5697.
(b) Zhou, J. Y.; Lu, G. D.; Wu, S. H. Synth. Commun. 1992, 22, 481.
26 Kunz, T.; Reibig, H. U. Liebigs Ann. Chem. 1989, 891.
27 Lee, A. S. Y.; Lin, L. S. Tetrahedron Lett. 2000, 41, 8803.
28 Bieber, L. W.; Silva, M. F.; Costa, R. C.; Silva, L. O. S. Tetrahedron Lett. 1998, 39, 3655.
29 (a) Jairaj, V.; Burton, D. J. J. Fluorine Chem. 2001, 111, 233.
(b) Makosza, M.; Grela, K.; Fabianowski, W. Tetrahedron 1996, 52, 9575.
(c) Marquez, F.; Montoro, R.; Llebaria, A.; Lago, E.; Molins, E.; Delgado, A. J. Org. Chem. 2002, 67, 308.
(d) Wang, D. K.; Dai, L. X.; Hou, X. L.; Zhang, Y. Tetrahedron Lett.1996, 37, 4187.
(e) Rubsam, F.; Seck, S.; Giannis, A. Tetrahedron 1997, 53, 2823.
30 Keh, C. K.; Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 4026.
31 Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97.
32 Oda, Y.; Sumitomo Chem. Co. Private Commun.
33 Cripps, H. N.; Kiefer, E. F. Org. Synth. 1962, 42, 12.
34 (a) Wang, D. K.; Dai, L. X.; Zhang, X. L.; Hou, Y. Tetrahedron Lett. 1996, 37, 4187.
(b) Lu, W. S.; Chan, T. H. J. Org. Chem. 2000,65, 8589.
(c) Hanessian, S.; Yang, R. Y. Tetrahedron Lett. 1996, 37, 5273.
(d) kim, S. H.; Han, E. H. Tetrahedron Lett. 2000, 41, 6479.
(e) Lu, W.; Chan, T. H. J. Org. Chem. 2000, 65, 8589.
35 Rubsam, F.; Seck, S.; Giannis, A. Tetrahedron 1997, 53, 2823.
36 Estevam, H. S.; Bierber, L. W. Tetrahedron Lett. 2003, 44, 667.
37 Chan, T. H.; Li, C. J.; Wei, Z. Y. Chem. Commun. 1990, 505.
38 Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181.
39 Durant, A.; Delplancke, J. L.; Winand, R.; Reisse, J. Tetrahedron Lett. 1995, 36, 4257.
40 (a)Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191.
(b) Nokami, J.; Wakabayashi, S.; Okawara, R. Chem. Lett. 1984, 869.
(c) Uneyama, K.; Kamaki, N.; Moriya, A.; Torii, S. J. Org. Chem. 1985, 50, 5396.
41 Wu, S. H.; Huang, B. Z.; Zhu, T. M.; Yiao, D. Z.; Chi, Y. L. Acta Chim. Sinica 1990, 48, 372 (in Chinese).
(吴世晖, 黄邦洲, 朱天民, 姚丹姝, 初永亮, 化学学报, 1990, 48, 372.)
42 Petrier, C.; Einhorn, J.; Luche, J. L. Tetrahedron 1985, 11, 1449.
43 (a) Wang, Z. Y.; Zha, Z. G.; Zhou, C. L. Org. Lett. 2002, 4, 1683.
(b) Zha, Z. G.; Wang, Y. S.; Yang, Y.; Zhang, L.; Wang, Z. Y. Green Chem. 2002, 4, 578.
44 Nokami, J.; Wakabayashi, S.; Okawara, R. Chem. Lett. 1984, 869.
45 Zhou, J. Y.; Chen, A. G.; Wu, S. H. Chem. Commun. 1994, 2783.
46 Nokami, J.; Tamkaoka, T.; Ogawa, H.; Wakabayash, S. Chem. Lett. 1986, 541.
47 Uneyama, K.; Ueda, K.; Torii, S. Chem. Lett. 1986, 1201.
48 Talaga, P.; Schaffer, M.; Benezra, C.; Stampf, J. L. Synthesis 1990, 530.
49 Zhou, J. Y.; Lu, G. D.; Wu, S. H. Synth. Commun. 1992, 22, 481.
50 Chan, T. H.; Li, C. J.; Wei, Z. Y. Chem. Commun. 1990, 1459.
51 Li, C. J. Ph.D. Dissertation, 1992.
52 Takahara, J. P.; Masuyama, Y.; Kurusu, Y. J. Am. Chem. Soc.1992, 114, 2577.
53 (a) Kundu, A.; Prabhakar, S.; Vairamini, M.; Roy, S. Organometallics 1997, 16, 4796.
(b) Samoshin, V. V.; Grenyachinskiy, D. E.; Smith, L. L.; Bliznets, I. V.; Gross, P. H. Tetrahedron Lett. 2002, 43, 6329.
54 Tan, X. H.; Shen, B.; Liu, L.; Guo, Q. X. Tetrahedron Lett.2002, 43, 9373.
55 Tan, X. H.; Shen, B.; Deng, W.; Zhao, Hi.; Liu, L.; Guo, Q. X.Org. Lett. 2003, 5, 1833.
56 Sinha, P.; Roy, S. Chem. Commun. 2001, 1798.
57 (a)Masuyama, Y.; Ito, T.; Tachi, K.; Ito, A.; Kurusu, Y. Chem. Commun. 1999, 1261.
(b) Masuyama, Y.; Ito, A.; Fukuzawa, M.; Terada, K.; Kurusu, Y. Chem.Commun. 1998, 2025.
(c) Chung, W. J.; Higashiya, S.; Welch, J. T. Tetrahedron Lett. 2002, 43, 5801.
(d) Loh, T. P.; Yin, Z.; Song, H. Y.; Tan, K. L. Tetrahedron Lett.2003, 44, 911.
(e) Li, C. J.; Chen, D. L.; Lu, Y. Q.; Haberman, X.; Majue, J. T. Tetrahedron 1998, 54, 2347.
(f) Yasuyama, Y.; Ito, A.; Kurusu, Y. Chem. Commun. 1998, 315.
58 Yanagisawa, A.; Inoue, H.; Morodone, M.; Yamamoto, H. J. Am.Chem. Soc. 1993, 115, 10356.
59 Kamble, R. M.; Singh, V. K. Tetrahedron Lett. 2001, 42, 7525.
60 Keck, G. E.; Tarbet, H. K.; Geraci, L. S. J. Am. Chem. Soc.1993, 85, 8467
61 Yanagisawa, A.; Nakasima, H.; Ishiba, A.; Yamamoto, H. J. Am.Chem. Soc. 1996, 118, 4723.
62 Yasuda, M.; Sugawa, Y.; Yamamoto, A.; Shibata, I.; Baba, A. Tetrahedron Lett. 1996, 37, 5951.
63 Yadav, J. S.; Reddy, B. V. S.; Krishna, A. D.; Sadasiv, K.; Chary, C. J. Chem. Lett. 2003, 32, 248.
64 Basavaiah, D.; Sreenivasulu, B. Tetrahedron Lett. 2002, 43, 2987.
65 Aspinall, H. C.; Greeves, N.; McIver, E. G. Tetrahedron Lett. 1998, 39, 9283.
66 (a) Aspinall, H. C.; Bissett, J. S.; Greeves, N.; Levin, D. Tetrakedron Lett. 2002, 43, 319.
(b) Liu, J.; Wong, C.-H. Tetrahedron Lett. 2002, 43, 3915.
67 Masuyama, Y.; Suga, T.; Watabe, A.; Kususu, Y. Tetrahedron Lett. 2003, 44, 2845.
68 Molle, G.; Bauer, P. J. Am. Chem. Soc. 1982, 104, 3481.
69 Wakefield, B. J. Organomagnesium, Methods in Organic Synthesis, Academic Press, San Diego, 1995.
70 (a) Li, C. J.; Zhang, W. C. J. Am. Chem. Soc. 1998, 120, 9102.
(b) Zhang, W. C.; Li, C. J. J. Org. Chem. 1999, 64, 3230.
71 Gilman, H.; McGlumphy, J. H. Bull. Soc. Chim. Fr. 1928, 43, 1322.
72 Sarangi, C.; Nayak, A.; Nanda, B.; Das, N. B. Tetrahedron Lett. 1995, 36, 7119.
73 Wada, M.; Fukuma, T.; Morioka, M.; Tukahashi, T.; Miyoshi, N.Tetrahedron Lett. 1997, 38, 8045.
74 Basu, M. K.; Bani, B. K. Tetrahedron. Lett. 2001, 42, 187.
75 (a) Molander, G. A.; Mckie, J. A. J. Org. Chem. 1991, 56, 4122.
(b) Molander, G. A; Huerou, Y. L.; Brown, G. A. J. Org. Chem. 2001, 66, 4511.
76 Curran, D. P.; Gu, X.; Zhang, W.; Dowd, P. Tetrahedron 1997, 53, 9023.
77 Kunisima, M.; Nakata, D.; Tanaka, S.; Hioki, K.; Tani, S. Tetrahedron 2000, 56, 9927.
78 Yanada, R.; Negoro, N.; Okaniwa, M.; Ibuka, T. Tetrahedron1999, 55, 13947.
79 Fan, X.; Zhang, Y. Tetrahedron Lett. 2002, 43, 5475.
80 Laskar, D. D.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 2001, 42, 7883.
81 Wada, M.; Akiba, K. Tetrahedron Lett. 1985, 26, 4211.
82 Wada, M.; Ohki, H.; Akiba, K. Tetrahedron Lett. 1986, 27, 4771.
83 Wada, M.; Ohki, H.; Akiba, K. J. Chem. Soc., Chem. Commun.1987, 708.
84 (a) Wada, M.; Ohki, H. Bull. Chem. Soc. Jpn. 1990, 67, 1738.
(b) Wada, M.; Honna, M.; Kuramoto, Y.; Miyoshi, N. Bull. Chem. Soc. Jpn. 1997, 2265.
85 Wada, M.; Honna, M.; Kuramoto, Y.; Miyoshi, N. Tetrahedron Lett. 1997, 38, 8045.
86 Fukama, T.; Lock, S.; Miyoshi, N.; Wada, M. Chem. Lett. 2000, 376.
87 Miyoshi, N.; Nishio, M.; Murakami, S.; Fukama, T.; Wada, M. Bull. Chem. Soc. Jpn. 2000, 73, 689.
88 Wang, Z. Y.; Yuan, S. Z.; Li, C. J. Tetrahedron Lett. 2002, 43, 5097.
89 Takai, K.; Ikawa, Y. Org. Lett. 2002,4, 1727.
90 Tsuji, T.; Usugi, S.; Yorimistu, H.; Shinokubo, H.; Matsubara,S.; Oshima, K. Chem. Lett. 2002, 2.
91 Li, C. J.; Meng, Y.; Yi, X. H.; Ma, J.; Chan, T. H. J. Org. Chem. 1997, 62, 8632.
92 Li, C. J.; Meng, Y.; Yi, X. H. J. Org. Chem. 1998, 63, 7498.
93 Takai, K.; Ueda, T.; Hayashi, T.; Moriwake, T. Tetrahedron Lett. 1996, 37, 7049.
94 Bandini, M.; Cozzi, P. G.; Umani, R. A. Tetrahedron 2001, 57, 835.
95 Nishikawa, T.; Nakamura, T.; Kakiya, H.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1999, 40, 6613.
96 Wang, W.; Shi, L.; Huang, Y. Tetrahedron 1990, 46, 3315.
97 Ren, P. D.; Jin, Q. H.; Yao, Z. P. Synth. Commun. 1997, 27, 2761.
98 Li, L. H.; Chan, T. H. Tetrahedron Lett. 2000, 41, 5009.
99 (a) Watahiki, T.; Oriyama, T. Tetrahedron Lett. 2002, 43, 8959.
(b) Itami, K.; Kamei, T.; Mineno, M.; Yoshida, J. Chem. Lett. 2002, 1084.
(c) Asao, N.; Shibuo, A.; Itagaki, Y.; Jourdan, F.; Maruoku, K. Tetrahedron Lett. 1998, 39, 3177.
100 (a) Kitayama, K.; Tsuji, H.; Uozami, Y.; Hayashi, T. Tetrahedron Lett. 1996, 37, 4169.
(b) Ogawa, C.; Sugiura, M.; Kobayashi, S. Chem. Commun. 2003, 192 .
(c) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron1999, 55, 977.
(d) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahedron Lett. 1998, 39, 2767.
101 Aoyama, N.; Hamada, T.; Manabe, K.; Kobayashi, S. Chem. Commun.2003, 276.
102 Wieland, L. C.; Zerth, H. M.; Mohan, R. S. Tetrahedron Lett. 2002, 43, 4597.
103 Yada, V. J. S.; Reddy, B. V. S.; Madhuri, C.; Sabitha, G. Chem. Lett. 2001, 18.
104 Yasuda, M.; Onishi, Y.; Ito, T.; Baba, A. Tetrahedron Lett. 2000, 41, 2425.
105 (a) Akiyama, T.; Iwai, J. Tetrahedron Lett. 1997, 38, 853.
(b) Akiyama, T.; Iwai, J.; Sugano, M. Tetrahedron 1999, 55, 7499.
106 Chan, T. H.; Yang, Y. Tetrahedron Lett. 1999, 40, 3863.
107 Zhou, J. Y.; Jia, Y.; Sun, G. F.; Wu, S. H. Synth. Commun. 1997, 27, 1899.
108 Li, C. J.; Meng, Y. J. Am. Chem. Soc. 2000, 122, 9538.
109 Huang, T.; Meng, Y.; Venkatraman, S.; Wang, D.; Li, C. J. J. Am. Chem. Soc. 2001, 123, 7451.
110 (a) Tanaka, H.; Nakahata, S.; Watanabe, H.; Zhao, J.; Kuroboshi, M.;Torri, S. Inorg. Chim. Acta 1996, 296, 204.
(b) Hanawa, H.; Maekawara, N.; Maruoka, K. Tetrahedron Lett. 1999, 40, 8379.
111 (a) Khan, R. H.; Rao, T. S. R. J. Chem. Res. 1998, 202.
(b) Schrekker, H. S.; Bolster, M. W. G.; Orru, R. V. A.; Wessjohann, L.A. J. Org. Chem. 2002, 67, 1975.
112 Thadani, A. N.; Batey. R. A. Org. Lett. 2002, 22, 3827.
113 (a) Souza, J. C.; Petrier, C.; Luche, J. L. J. Org. Chem. 1988, 53, 1212.
(b) Cyenes, F.; Bergmann, K. E.; Welch, J. T. J. Org. Chem. 1998, 63, 2824.
114 Luche, J. L.; Petrier, C.; Einhorn, J. Tetrahedron. 1985, 11, 1449.
115 See corresponding reference cited above.
116 (a) Li, C. J.; Meng, Y.; Yi, X. H.; Ma, J.; Chan, T, H. J. Org. Chem. 1997, 62, 8632.
(b) Zhang, W. C.; Li, C. J. J. Org. Chem. 1999, 64, 3230.
117 Loh, T, P.; Xu, J. Tetrahedron Lett. 1999, 40, 2431.
118 (a) Takahara, J. P.; Masuyama, Y.; Kurasu, Y. J. Am. Chem. Soc.1992, 114, 2577.
(b) Masuyama, Y.; Takahara, J. P.; Kurusu, Y. J. Am. Chem. Soc. 1988, 110, 4473.
119 Issac, M. B.; Chan, T. H. Tetrahedron Lett. 1995, 36, 8957.
120 (a) Tan, K. T.; Chng, S. S.; Cheng, H. S.; Loh, T. P. J. Am. Chem.Soc. 2003, 125, 2958.
(b) Araki, S.; Ito, H.; Katsumura, N.; Butsugan, Y. J. Organomet. Chem. 1989, 369, 291.
(c) Araki, S.; Katsurmura, N.; Butsugan, Y. J. Organomet. Chem. 1991, 415, 7.
121 For a review, see: Paquette, L. A. In Green Chemistry, Fronters inBenign Chemical Syntheses and Processes, Eds.: Anastas, P.; Williamson, T. C., Oxford University Press, New York, 1998.
For more detailsed information, see: (a) Paquette, L. A.; Rothharr, R. R.; Isaac, M.; Rogers, L. M.; Rogers, R. D. J. Org. Chem. 1998, 63, 5463.
(b) Lobben, P. C.; Paquette, L. A. J. Org. Chem. 1998, 63, 6990.
(c) Paquette, L. A.; Mendez-Andino, J. L. J. Org. Chem. 1998, 63, 9061.
(d) Paquette, L. A.; Mitzel, T. M.; Isaac, M. B.; Crasto, C. F.; Schomer, W. W. J. Org. Chem. 1997, 62, 4293.
(e) Paquette, L. A.; Bennett, G. D.; Chhatriwalla, A.; Isaac, M. B. J.Org. Chem. 1997, 62, 2270.
(f) Issac, M. B.; Paquette, L. A. J. Org. Chem. 1997, 62, 5333.
(g) Bernardelli, P.; Paquette, L. A. J. Org. Chem. 1997, 62, 8285.
(h) Paquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917.
(i) Paquette, L. A.; Mitzel, T. M. J. Org. Chem. 1996, 61, 8799.
(j) Paquette, L. A.; Stepanian, M.; Mallavadhani, U. V.; Cutarelli, T. D.; Lowinger, T. B.; Klemeyer, H. J. J. Org. Chem. 1996, 61, 7492.
122 Chan, T. H.; Isaac, M. Tetrahedron Lett. 1996.
123 Chan, T. H.; Li, C. J. Can. J. Chem. 1992,70, 2726.
124 Waldmann. H. Synlett. 1990, 627.
125 Bandini, M.; Cozzi, P. G.; Umani, R. A. Tetrahedron 2001, 57, 835.
126 Yanagisawa, A.; Nakasima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723.
127 (a) Chan, T. H.; Li, C. J. Chem. Commun. 1992, 747.
(b) Dardon, A.; Merino, P.; Orduna, J. Tetrahedron Lett. 1991, 32, 3247.
(c) Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7939.
(d) Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500.
(e) Gao, J.; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714.
(g) Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228.
(h) Pernner, R. G.; Binder, W. H.; Schemid, W. Libigs Ann. Chem. 1994, 73.
(i) Binder, W. H.; Prenner, R. H.; Schmid, W. Tetrahedron 1994, 50, 749.
128 Schmid, W.; Whitesides. G. M. J. Am. Chem. Soc. 1991, 113, 6674.
129 LI, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995,36, 2721.
130 Yang, Z. Y.; Burton, D. J. J. Org. Chem. 1991, 56, 1037.
131 Some other important work, see: (a) Song, L.-C.; Fan, H.-T.; Hu, Q.-M. Chin. J. Org. Chem. 2001, 21, 713.
(b) Zhu, Z.-Q.; Zeng, J.-Q. Chin. J. Org. Chem. 2001, 21, 1095.
(c) Liao, L.-A.; Li, Z.-M. Chin. J. Org. Chem. 2000, 20, 306.
(d) Yuan, Y.-F.; Cao, Z.; Hu, A.-G.; Wang, J.-T. Chin. J. Org. Chem. 2000, 20, 269.
(e) Ren, P.-D.; Pan, S.-F.; Dong, T.-W.; Wu, S.-H. Chin. J. Chem. 1996, 14, 462.
(f) Zhou, J.-Y.; Sun, G.-F.; Zhang, M.-F.; Jia, Y.; Wu, S.-H. Chin. J. Chem. 1997, 15, 361.
(g) Deng, D.-L.; Lu, Z.-H.; Wu, K. Chin. J. Org. Chem. 1996, 16, 462.
(h) Zou, C.-L.; Zha, Z.-G.;Wang, Z.-Y.; Wu, J.-H.; Zhang, J.-H. Chin. J. Chem. 2002, 20, 718.
(i) Zha, Z.-G.; Xie, Z; Zhou, C.-L.; Wang, Z.-Y.; Wang, Y.-S. Chin. J. Chem. 2002, 20, 1477.

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各种金属参与的水相Barbier-Type反应