Zinc-mediated radical reactions of per- (or poly)fluorophenyl aromatic aldimines in aqueous media

Synthesis

Volumn , Issue 5, 2004, Pages 683-691

  Liu, Xinyuan ^a,b   Zhu, Shizheng ^b   Wang, Shaowu ^a  

^a ANHUI NORMAL UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Alkyl halides; Imines; Polyfluororinated amines; Radical reactions; Zinc

Indexed keywords

ADDITION REACTIONS; AROMATIC COMPOUNDS; NITROGEN COMPOUNDS; REACTION KINETICS; SOLUTIONS; SUBSTITUTION REACTIONS; THERMAL EFFECTS; ZINC;

AQUEOUS MEDIA; INTERMOLECULAR ADDITIONS; ROOM TEMPERATURE; SINGLE-ELECTRON-TRANSFER RADICAL INITIATOR;

SYNTHESIS (CHEMICAL);

AMINE; BENZENE DERIVATIVE; FLUORINE; IMINE; PERFLUORO COMPOUND; ZINC;

ADDITION REACTION; AIR; AQUEOUS SOLUTION; AROMATIZATION; ARTICLE; ATMOSPHERE; ELECTRON TRANSPORT; ENERGY YIELD; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MECHANICS; REACTION ANALYSIS; ROOM TEMPERATURE;

EID: 1942489239     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-816004     Document Type: Article

References (58)

1. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895.
2. Bloch, R. Chem. Rev. 1998, 98, 1407.
3. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
4. Garner, P. P.; Parker, D. T.; Gajewski, J. J.; Lubineau, A.; Angé, J.; Queneau, Y.; Beletskaya, I. P.; Cheprakov, A. V.; Fringuelli, F.; Piermatti, O.; Pizzo, F.; Kobayashi, S. Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic Professional: London, 1998.
5. For reviews, see: (a) Li, C. J. Chem. Rev. 1993, 93, 2023. (b) Lubineau, A.; Angé, J.; Queneau, Y. Synthesis 1994, 741. (c) Li, C. J. Tetrahedron 1996, 52, 5643.
6. For reviews, see: (a) Li, C. J. Chem. Rev. 1993, 93, 2023. (b) Lubineau, A.; Angé, J.; Queneau, Y. Synthesis 1994, 741. (c) Li, C. J. Tetrahedron 1996, 52, 5643.
7. For reviews, see: (a) Li, C. J. Chem. Rev. 1993, 93, 2023. (b) Lubineau, A.; Angé, J.; Queneau, Y. Synthesis 1994, 741. (c) Li, C. J. Tetrahedron 1996, 52, 5643.
8. (a) Naito, T. Heterocycles 1999, 50, 505.
9. (b) Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543.
10. (a) Hart, D. J.; Seely, F. J. J. Am. Chem. Soc. 1988, 110, 1631.
11. (b) Miyabe, H.; Ueda, M.; Naito, T. J. Org. Chem. 2000, 65, 5043.
12. Bertrand, M.; Feray, L.; Nouguier, R.; Perfetti, P. J. Org. Chem. 1999, 64, 9189.
13. Ueda, M.; Miyabe, H.; Nishimura, A.; Sugino, H.; Naito, T. Tetrahedron: Asymmetry 2003, 14, 2857.
14. Miyabe, H.; Ueda, M.; Naito, T. Chem. Commun. 2000, 2059.
15. Chan, T. H.; Lu, W. Tetrahedron Lett. 1998, 39, 8605.
16. Chan, T. H.; Lu, W. J. Org. Chem. 2000, 65, 8589.
17. For a recent example of the successful aqueous allylation of imines, see: Kobayashi, S.; Busujima, T.; Nagayama, S. Chem. Commun. 1998, 19.
18. Hudlicky, M. Chemistry of Organic Fluorine Compounds; Ellis Horwood: Chichester, 1992.
19. Welch, J. T. Tetrahedron 1987, 43, 3123.
20. Organofluorine Chemistry, Principles and Commercial Applications; Banks, R. E.; Smart, B. E.; Tatlow, J. C., Eds.; Plenum: New York, 1994.
21. Loupy, A.; Petit, A.; Bonnet-Delpon, D. J. Fluorine Chem. 1995, 75, 215.
22. Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem. Int. Ed. 1998, 37, 2581.
23. Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161.
24. Robertson, G. M. Comprehensive Organic Synthesis, Vol. 3; Pergamon: Oxford, 1991, 579-582.
25. (a) Reinhart, K. L.; Harada, K.-i.; Namikoshi, M.; Chen, C.; Harvis, C. A.; Munro, M. H. G.; Blunt, J. W.; Mulligan, P. E.; Beasley, V. R.; Dahelm, A. M.; Carmichael, W. W. J. Am. Chem. Soc. 1988, 110, 8557.
26. (b) de Silva, E. D.; Williams, D. E.; Anderson, R. J.; Klix, H.; Holmes, C. F. B.; Allen, T. M. Tetrahedron Lett. 1992, 33, 1561.
27. (c) Fusetani, N.; Matsunaga, S.; Matsumoto, H.; Takebayshi, Y. J. Am. Chem. Soc. 1990, 112, 7053.
28. (d) Coleman, J. E.; de Silva, E. D.; Kong, F.; Andersen, R. J.; Allen, T. M. Tetrahedron 1995, 51, 10653.
29. (e) Ambrosio, M. D.; Guerriero, A.; Debitus, C.; Pietra, F. Helv. Chim. Acta 1996, 79, 51.
30. Petranyi, G.; Ryder, N. S.; Stütz, A. Science 1984, 224, 1239.
31. (a) Burgess, K.; Ohlmeyer, M. J. J. Org. Chem. 1991, 56, 1027.
32. (b) Hagihara, M.; Anthony, N. J.; Stout, T. J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6568.
33. (c) Vedejs, E.; Gringras, M. J. Am. Chem. Soc. 1994, 116, 579.
34. (d) Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004.
35. (e) Noyori, R. Asymmertric Catalysis in Organic Synthesis; Wiley: New York, 1994.
36. (a) Chan, T. H.; Lu, W. J. Org. Chem. 2000, 65, 8589.
37. (b) Vilaivan, T.; Winotapan, C.; Shinada, T.; Ohfune, Y. Tetrahedron Lett. 2001, 42, 9073.
38. (c) Hilt, G.; Smolko, K. I.; Waloch, C. Tetrahedron Lett. 2002, 43, 1437.
39. (d) Patel, S. J.; Jamison, T. F. Angew. Chem. Int. Ed. 2003, 42, 1364.
40. (a) Vilaivan, T.; Winotapan, C.; Shinada, T.; Ohfune, Y. Tetrahedron Lett. 2001, 42, 9073.
41. (b) Lu, W.; Chan, T. H. J. Org. Chem. 2000, 65, 8589.
42. (c) Chan, T. H.; Lu, W. Tetrahedron Lett. 1998, 39, 8605.
43. (d) Kumar, H. M. S.; Anjaneyulu, S.; Reddy, E. J.; Yadav, J. S. Tetrahedron Lett. 2000, 41, 9311.
44. (e) Loh, T.-P.; Diana, S.-C.; Xu, K.-C.; Sim, K.-Y. Tetrahedron Lett. 1997, 38, 865.
45. (f) Choucair, B.; Léon, H.; Miré, M.-A.; Lebreton, C.; Mosset, P. Org. Lett. 2000, 2, 1851.
46. (g) Bossard, F.; Dambtin, V.; Beuchet, P.; Mosset, P. Tetrahedron Lett. 1995, 36, 6055.
47. (h) Beuchet, P.; Le Marrec, N.; Mosset, P. Tetrahedron Lett. 1992, 33, 5959.
48. (i) Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766.
49. (j) Pitts, M. R.; Harrison, J. R.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1 2001, 955.
50. (k) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4095.
51. (k) Fujiwara, N.; Yamamoto, Y. Tetrahedron Lett. 1998, 39, 4729.
52. Miyabe, H.; Nishimura, A.; Ueda, M.; Naito, T. Chem. Commun. 2002, 1454.
53. Hanessian, S.; Yang, R. Y. Tetrahedron Lett. 1996, 5273.
54. (a) Li, C. J. Chem. Rev. 1993, 93, 2023.
55. (b) Lubineau, A.; Angé, J.; Queneau, Y. Synthesis 1994, 741.
56. (a) Li, C. J. Tetrahedron 1996, 52, 5643.
57. Keh, C. C. K.; Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 4062.
58. Li, A. W.; Xu, B.; Zhu, S. Z. J. Fluorine Chem. 1994, 68, 145.