Metal-mediated Barbier-type carbonyl allylation under solvent-free conditions

Synthetic Communications

Volumn 28, Issue 16, 1998, Pages 2999-3009

  Yi, Xiang Hui ^a   Haberman, John X ^a   Li, Chao Jun ^a  

^a Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CARBONYL DERIVATIVE; HALIDE; INDIUM; METAL; SOLVENT; TIN; ZINC;

ARTICLE; CHEMICAL REACTION; MOLECULAR INTERACTION; POLYMERIZATION;

EID: 0031880588     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808004878     Document Type: Article

References (19)

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2. Blomberg, C. The Barbier Reaction and Related One-Step Processes; Springer-Verlag, 1993.
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4. Frankland, E. Ann. 1849, 71, 171; Reformatsky, A. Ber. 1887, 20, 1210.
5. Barbier, P. Compt. Rend. 1899, 128, 110; Grignard, V. Compt. Rend. 1900, 130, 1322.
6. Barbier, P. Compt. Rend. 1899, 128, 110; Grignard, V. Compt. Rend. 1900, 130, 1322.
7. Wittig, G. Newer Methods of Preparative Organic Chemistry 1948, 571.
8. For some examples of indium mediated reactions, see: Chao, L. C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253; Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831; Araki, S.; Katsumura, N.; Ito, H.; Butsugan, Y. Tetrahedron Lett. 1989, 30, 1581. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Paquette, L.; Mitzel, T. M. J. Am. Chem. Soc., 1996, 118, 1931; Li, C. J.; Chen, D. L.; Lu, Y. Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry, 1996, 7, 1535.
9. For some examples of indium mediated reactions, see: Chao, L. C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253; Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831; Araki, S.; Katsumura, N.; Ito, H.; Butsugan, Y. Tetrahedron Lett. 1989, 30, 1581. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Paquette, L.; Mitzel, T. M. J. Am. Chem. Soc., 1996, 118, 1931; Li, C. J.; Chen, D. L.; Lu, Y. Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry, 1996, 7, 1535.
10. For some examples of indium mediated reactions, see: Chao, L. C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253; Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831; Araki, S.; Katsumura, N.; Ito, H.; Butsugan, Y. Tetrahedron Lett. 1989, 30, 1581. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Paquette, L.; Mitzel, T. M. J. Am. Chem. Soc., 1996, 118, 1931; Li, C. J.; Chen, D. L.; Lu, Y. Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry, 1996, 7, 1535.
11. For some examples of indium mediated reactions, see: Chao, L. C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253; Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831; Araki, S.; Katsumura, N.; Ito, H.; Butsugan, Y. Tetrahedron Lett. 1989, 30, 1581. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Paquette, L.; Mitzel, T. M. J. Am. Chem. Soc., 1996, 118, 1931; Li, C. J.; Chen, D. L.; Lu, Y. Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry, 1996, 7, 1535.
12. For some examples of indium mediated reactions, see: Chao, L. C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253; Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831; Araki, S.; Katsumura, N.; Ito, H.; Butsugan, Y. Tetrahedron Lett. 1989, 30, 1581. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Paquette, L.; Mitzel, T. M. J. Am. Chem. Soc., 1996, 118, 1931; Li, C. J.; Chen, D. L.; Lu, Y. Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry, 1996, 7, 1535.
13. For some examples of indium mediated reactions, see: Chao, L. C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253; Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831; Araki, S.; Katsumura, N.; Ito, H.; Butsugan, Y. Tetrahedron Lett. 1989, 30, 1581. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Paquette, L.; Mitzel, T. M. J. Am. Chem. Soc., 1996, 118, 1931; Li, C. J.; Chen, D. L.; Lu, Y. Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry, 1996, 7, 1535.
14. For some examples of indium mediated reactions, see: Chao, L. C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253; Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831; Araki, S.; Katsumura, N.; Ito, H.; Butsugan, Y. Tetrahedron Lett. 1989, 30, 1581. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Paquette, L.; Mitzel, T. M. J. Am. Chem. Soc., 1996, 118, 1931; Li, C. J.; Chen, D. L.; Lu, Y. Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry, 1996, 7, 1535.
15. For some examples of indium mediated reactions, see: Chao, L. C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253; Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831; Araki, S.; Katsumura, N.; Ito, H.; Butsugan, Y. Tetrahedron Lett. 1989, 30, 1581. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Paquette, L.; Mitzel, T. M. J. Am. Chem. Soc., 1996, 118, 1931; Li, C. J.; Chen, D. L.; Lu, Y. Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry, 1996, 7, 1535.
16. For some examples of indium mediated reactions, see: Chao, L. C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253; Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831; Araki, S.; Katsumura, N.; Ito, H.; Butsugan, Y. Tetrahedron Lett. 1989, 30, 1581. Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; Paquette, L.; Mitzel, T. M. J. Am. Chem. Soc., 1996, 118, 1931; Li, C. J.; Chen, D. L.; Lu, Y. Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216; Li, X. R.; Loh, T. P. Tetrahedron: Asymmetry, 1996, 7, 1535.
17. For a recent review, see: Wirth, T. Angew. Chem. Int. Ed. Engl. 1996, 35, 61.
18. Far a recent review about allylation reaction of carbonyl compounds with allylmetal reagents, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
19. Molle, G.; Bauer, P. J. Am. Chem. Soc. 1982, 104, 3481.