Organic reactions in water and other alternative media: Metal-mediated carbon-carbon bond formations

ACS Symposium Series

Volumn 819, Issue , 2002, Pages 178-190

  Li, Chao Jun ^a   Haberman, John X ^a   Keh, Charlene C K ^a   Yi, Xiang Hui ^a   Meng, Yue ^a   Hua, Xiao Gang ^a   Venkatraman, Sripathy ^a   Zhang, Wen Chun ^a   Nguyen, Tien ^a   Wang, Dong ^a   Huang, Taisheng ^a   Zhang, Jianheng ^a  

^a Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042367143     PISSN: 00976156     EISSN: None     Source Type: Book Series    
DOI: None     Document Type: Article

References (46)

1. Green Chemistry, Frontiers in Benign Chemical Syntheses and Processes, Eds. Anastas, P. T.; Williamson, T. C. Oxford University Press, New York, 1998.
2. Frankland, E. Ann. 1849, 71, 171; Reformatsky, A. Ber. 1887, 20, 1210.
3. Frankland, E. Ann. 1849, 71, 171; Reformatsky, A. Ber. 1887, 20, 1210.
4. Barbier, P. Compt. Rend. 1899, 128, 110; Grignard, V. Compt. Rend. 1900, 130, 1322.
5. Barbier, P. Compt. Rend. 1899, 128, 110; Grignard, V. Compt. Rend. 1900, 130, 1322.
6. Wittig, G. Newer Methods of Preparative Organic Chemistry 1948, 571.
7. Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Organometallics 1983, 2, 191.
8. Petrier, C.; Luche, J. L. J. Org. Chem. 1985, 50, 910.
9. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Paquette, L. A. in Green Chemistry, Frontiers in Benign Chemical Syntheses and Processes, Eds. Anastas, P. and Williamson, T. C. Oxford University Press, New York 1998; Prenner, R. H.; Binder, W. H.; Schmid, W. Libigs Ann. Chem. 1994, 73; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry 1996, 7, 1535.
10. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Paquette, L. A. in Green Chemistry, Frontiers in Benign Chemical Syntheses and Processes, Eds. Anastas, P. and Williamson, T. C. Oxford University Press, New York 1998; Prenner, R. H.; Binder, W. H.; Schmid, W. Libigs Ann. Chem. 1994, 73; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry 1996, 7, 1535.
11. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Paquette, L. A. in Green Chemistry, Frontiers in Benign Chemical Syntheses and Processes, Eds. Anastas, P. and Williamson, T. C. Oxford University Press, New York 1998; Prenner, R. H.; Binder, W. H.; Schmid, W. Libigs Ann. Chem. 1994, 73; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry 1996, 7, 1535.
12. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Paquette, L. A. in Green Chemistry, Frontiers in Benign Chemical Syntheses and Processes, Eds. Anastas, P. and Williamson, T. C. Oxford University Press, New York 1998; Prenner, R. H.; Binder, W. H.; Schmid, W. Libigs Ann. Chem. 1994, 73; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry 1996, 7, 1535.
13. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Paquette, L. A. in Green Chemistry, Frontiers in Benign Chemical Syntheses and Processes, Eds. Anastas, P. and Williamson, T. C. Oxford University Press, New York 1998; Prenner, R. H.; Binder, W. H.; Schmid, W. Libigs Ann. Chem. 1994, 73; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry 1996, 7, 1535.
14. Wada, M.; Ohki, H.; Akiba, K. Y. J. Chem. Soc., Chem. Commun. 1987, 708; Katritzky, A. R.; Shobana, N.; Harris, P. A. Organometallics 1992, 11, 1381.
15. Wada, M.; Ohki, H.; Akiba, K. Y. J. Chem. Soc., Chem. Commun. 1987, 708; Katritzky, A. R.; Shobana, N.; Harris, P. A. Organometallics 1992, 11, 1381.
16. Li, C. J. Tetrahedron 1996, 52, 5643; Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
17. Li, C. J. Tetrahedron 1996, 52, 5643; Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
18. Wakefield, B. J. Organomagnesium Methods in Organic Chemistry, Academic Press, 1995.
19. Li, C. J.; Zhang, W. C. J. Am. Chem. Soc. 1998, 120, 9102.
20. Keh, C. C. K.; Li, C. J. unpublished results.
21. Li, C. J., PhD Dissertation, McGill University 1992.
22. Lexa, D.; Saveant, J. M.; Schaefer, H. J.; Su, K. B.; Vering, B.; Wang, D. L. J. Am. Chem. Soc. 1990, 112, 6162.
23. For recent reviews, see: Kendall, J. L.; Canelas, D. A.; DeSimone, J. M. Chem. Rev. 1999, 99, 543; Jessop, P. G.; Ikariya, T.; Noyori, R. Chem. Rev. 1999, 99, 475; Brennecke, J. F.; Chateauneuf, J. E. Chem. Rev. 1999 99, 433; Buelow, S.; Dell'Orco, P.; Morita, D.; Pesiri, D.; Birnbaum, E.; Borkowsky, S.; Brown, G.; Feng, S.; Luan, L. Morgenstern, D.; Tumas, W. in Green Chemistry, Frontiers in Benign Chemical Syntheses and Processes, Eds. Anastas, P. T.; Williamson, T. C. Oxford University Press, New York, 1998, p. 265.
24. For recent reviews, see: Kendall, J. L.; Canelas, D. A.; DeSimone, J. M. Chem. Rev. 1999, 99, 543; Jessop, P. G.; Ikariya, T.; Noyori, R. Chem. Rev. 1999, 99, 475; Brennecke, J. F.; Chateauneuf, J. E. Chem. Rev. 1999 99, 433; Buelow, S.; Dell'Orco, P.; Morita, D.; Pesiri, D.; Birnbaum, E.; Borkowsky, S.; Brown, G.; Feng, S.; Luan, L. Morgenstern, D.; Tumas, W. in Green Chemistry, Frontiers in Benign Chemical Syntheses and Processes, Eds. Anastas, P. T.; Williamson, T. C. Oxford University Press, New York, 1998, p. 265.
25. For recent reviews, see: Kendall, J. L.; Canelas, D. A.; DeSimone, J. M. Chem. Rev. 1999, 99, 543; Jessop, P. G.; Ikariya, T.; Noyori, R. Chem. Rev. 1999, 99, 475; Brennecke, J. F.; Chateauneuf, J. E. Chem. Rev. 1999 99, 433; Buelow, S.; Dell'Orco, P.; Morita, D.; Pesiri, D.; Birnbaum, E.; Borkowsky, S.; Brown, G.; Feng, S.; Luan, L. Morgenstern, D.; Tumas, W. in Green Chemistry, Frontiers in Benign Chemical Syntheses and Processes, Eds. Anastas, P. T.; Williamson, T. C. Oxford University Press, New York, 1998, p. 265.
26. For recent reviews, see: Kendall, J. L.; Canelas, D. A.; DeSimone, J. M. Chem. Rev. 1999, 99, 543; Jessop, P. G.; Ikariya, T.; Noyori, R. Chem. Rev. 1999, 99, 475; Brennecke, J. F.; Chateauneuf, J. E. Chem. Rev. 1999 99, 433; Buelow, S.; Dell'Orco, P.; Morita, D.; Pesiri, D.; Birnbaum, E.; Borkowsky, S.; Brown, G.; Feng, S.; Luan, L. Morgenstern, D.; Tumas, W. in Green Chemistry, Frontiers in Benign Chemical Syntheses and Processes, Eds. Anastas, P. T.; Williamson, T. C. Oxford University Press, New York, 1998, p. 265.
27. Kaupp, G. Angew. Chem. Int. Ed. Engl. 1994, 33, 1452; Wai, C. M.; Hunt F.; Ji, M.; Chen, X. J. Chem. Ed. 1998, 75, 1641.
28. Kaupp, G. Angew. Chem. Int. Ed. Engl. 1994, 33, 1452; Wai, C. M.; Hunt F.; Ji, M.; Chen, X. J. Chem. Ed. 1998, 75, 1641.
29. Hyatt, J. A. J. Org. Chem. 1984, 49, 5097.
30. Jeong, N.; Hwang, S. H.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549.
31. Tanko, J. M.; Blackert, J. F. Science 1994, 263, 203.
32. Hawthorne, S. B. Anal. Chem. 1990, 62, 633A; Hyatt, J. A. J. Org Chem. 1984, 49, 5097; Atwani, Z. Angew. Chem. Int. Ed. Engl. 1980, 19, 623; Laintz, K. E.; Hale, C. D.; Stark, P.; Rouquette, C. L.; Wilkinson, J. Anal. Chem. 1998, 70, 400; Isaacs, N. S.; Keating, N. J. Chem. Soc., Chem. Commun. 1992, 876.
33. Hawthorne, S. B. Anal. Chem. 1990, 62, 633A; Hyatt, J. A. J. Org Chem. 1984, 49, 5097; Atwani, Z. Angew. Chem. Int. Ed. Engl. 1980, 19, 623; Laintz, K. E.; Hale, C. D.; Stark, P.; Rouquette, C. L.; Wilkinson, J. Anal. Chem. 1998, 70, 400; Isaacs, N. S.; Keating, N. J. Chem. Soc., Chem. Commun. 1992, 876.
34. Hawthorne, S. B. Anal. Chem. 1990, 62, 633A; Hyatt, J. A. J. Org Chem. 1984, 49, 5097; Atwani, Z. Angew. Chem. Int. Ed. Engl. 1980, 19, 623; Laintz, K. E.; Hale, C. D.; Stark, P.; Rouquette, C. L.; Wilkinson, J. Anal. Chem. 1998, 70, 400; Isaacs, N. S.; Keating, N. J. Chem. Soc., Chem. Commun. 1992, 876.
35. Hawthorne, S. B. Anal. Chem. 1990, 62, 633A; Hyatt, J. A. J. Org Chem. 1984, 49, 5097; Atwani, Z. Angew. Chem. Int. Ed. Engl. 1980, 19, 623; Laintz, K. E.; Hale, C. D.; Stark, P.; Rouquette, C. L.; Wilkinson, J. Anal. Chem. 1998, 70, 400; Isaacs, N. S.; Keating, N. J. Chem. Soc., Chem. Commun. 1992, 876.
36. Hawthorne, S. B. Anal. Chem. 1990, 62, 633A; Hyatt, J. A. J. Org Chem. 1984, 49, 5097; Atwani, Z. Angew. Chem. Int. Ed. Engl. 1980, 19, 623; Laintz, K. E.; Hale, C. D.; Stark, P.; Rouquette, C. L.; Wilkinson, J. Anal. Chem. 1998, 70, 400; Isaacs, N. S.; Keating, N. J. Chem. Soc., Chem. Commun. 1992, 876.
37. For a recent review on solvent-free reactions, see: Dittmer, D. C. Chem. Ind. 1997, 779; Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213; Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 27, 10851; Varma, R. S. Green Chemistry 1999, 1, 43; Varma, R. S. in ACS Symp. Ser. 767, Green Chemical Syntheses and Processes, 292, (2000); Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025; Metzger, J. O. Angew. Chem. Int. Ed. Engl. 1998, 37, 2975.
38. For a recent review on solvent-free reactions, see: Dittmer, D. C. Chem. Ind. 1997, 779; Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213; Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 27, 10851; Varma, R. S. Green Chemistry 1999, 1, 43; Varma, R. S. in ACS Symp. Ser. 767, Green Chemical Syntheses and Processes, 292, (2000); Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025; Metzger, J. O. Angew. Chem. Int. Ed. Engl. 1998, 37, 2975.
39. For a recent review on solvent-free reactions, see: Dittmer, D. C. Chem. Ind. 1997, 779; Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213; Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 27, 10851; Varma, R. S. Green Chemistry 1999, 1, 43; Varma, R. S. in ACS Symp. Ser. 767, Green Chemical Syntheses and Processes, 292, (2000); Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025; Metzger, J. O. Angew. Chem. Int. Ed. Engl. 1998, 37, 2975.
40. For a recent review on solvent-free reactions, see: Dittmer, D. C. Chem. Ind. 1997, 779; Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213; Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 27, 10851; Varma, R. S. Green Chemistry 1999, 1, 43; Varma, R. S. in ACS Symp. Ser. 767, Green Chemical Syntheses and Processes, 292, (2000); Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025; Metzger, J. O. Angew. Chem. Int. Ed. Engl. 1998, 37, 2975.
41. For a recent review on solvent-free reactions, see: Dittmer, D. C. Chem. Ind. 1997, 779; Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213; Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 27, 10851; Varma, R. S. Green Chemistry 1999, 1, 43; Varma, R. S. in ACS Symp. Ser. 767, Green Chemical Syntheses and Processes, 292, (2000); Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025; Metzger, J. O. Angew. Chem. Int. Ed. Engl. 1998, 37, 2975.
42. For a recent review on solvent-free reactions, see: Dittmer, D. C. Chem. Ind. 1997, 779; Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213; Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 27, 10851; Varma, R. S. Green Chemistry 1999, 1, 43; Varma, R. S. in ACS Symp. Ser. 767, Green Chemical Syntheses and Processes, 292, (2000); Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025; Metzger, J. O. Angew. Chem. Int. Ed. Engl. 1998, 37, 2975.
43. For a recent review on solvent-free reactions, see: Dittmer, D. C. Chem. Ind. 1997, 779; Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213; Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 27, 10851; Varma, R. S. Green Chemistry 1999, 1, 43; Varma, R. S. in ACS Symp. Ser. 767, Green Chemical Syntheses and Processes, 292, (2000); Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025; Metzger, J. O. Angew. Chem. Int. Ed. Engl. 1998, 37, 2975.
44. Far a recent review about allylation reaction of carbonyl compounds with allylmetal reagents, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
45. Molle, G.; Bauer, P. J. Am. Chem. Soc. 1982, 104, 3481.
46. Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228.