Direct transfer of the sulfonylimino group of imino-λ3- bromane to N-heterocycles and trialkylamines: Synthesis of N-iminoammonium ylides under metal-free conditions

Organic Letters

Volumn 11, Issue 2, 2009, Pages 281-284

  Ochiai, Masahito ^a   Kawano, Yufuko ^a   Kaneaki, Takao ^a   Tada, Norihiro ^a   Miyamoto, Kazunori ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BROMINATED HYDROCARBON; HETEROCYCLIC COMPOUND; IMINE; METAL; NITROGEN; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; CHEMISTRY; KINETICS; SYNTHESIS; TEMPERATURE;

AMINES; HETEROCYCLIC COMPOUNDS; HYDROCARBONS, BROMINATED; IMINES; KINETICS; METALS; NITROGEN; QUATERNARY AMMONIUM COMPOUNDS; TEMPERATURE;

EID: 61449146170     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802383f     Document Type: Article

References (48)

1. Reviews: (a) Dauban, P.; Dodd, R. H. Synlett 2003, 1571.
2. (b) Muller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905.
3. (c) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
4. (d) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992.
5. (e) Hypervalent Iodine Chemistry; Wirth, T., Ed.; Topics in Current Chemistry 224; Springer: Berlin, 2003.
6. (f) Du Bois, J. Chemtracts 2005, 18, 1.
7. (g) Zhdankin, V. V. Sci. Synth. 2007, 31a (Chapter 31.4.1), 161.
8. For aziridination of olefins, see: (a) Mansuy, D.; Mahy, J.-P.; Dureault, A.; Bedi, G.; Battioni, P. J. Chem. Soc., Chem. Commun. 1984, 1161.
9. (b) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742.
10. (c) Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889.
11. (d) Au, S.-M; Huang, J.-S.; Yu, W.-Y.; Fung, W.-H.; Che, C.-M. J. Am. Chem. Soc. 1999, 121, 9120.
12. (e) Dauban, P.; Saniere, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707.
13. (f) Guthikonda, K.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 13672.
14. (g) Cui, Y.; He, C. J. Am. Chem. Soc. 2003, 125, 16202.
15. (h) Leung, S. K.-Y.; Tsui, W.-M.; Huang, J.-S.; Che, C.-M.; Liang, J.-L.; Zhu, N. J. Am. Chem. Soc. 2005, 127, 16629.
16. For C-H insertion, see: (a) Breslow, R.; Gellman, S. H. J. Am. Chem. Soc. 1983, 105, 6728.
17. (b) Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935.
18. (c) Fructos, M. R.; Trofimenko, S.; Diaz-Requejo, M. M.; Ferez, P. J. J. Am. Chem. Soc. 2006, 128, 11784.
19. (d) Fiori, K. W.; Du Bois, J. J. Am. Chem. Soc. 2007, 129, 562.
20. (e) Li, Z.; Capretto, D. A.; Rahaman, R.; He, C. Angew. Chem., Int. Ed. 2007, 46, 5184.
21. (f) Li, Z.; Capretto, D. A.; Rahaman, R.; He, C. J. Am. Chem. Soc. 2007, 129, 12058.
22. (a) Okuyama, T.; Takino, T.; Sueda, T.; Ochiai, M. J. Am. Chem. Soc. 1995, 117, 3360.
23. (b) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999; p 359.
24. N-Heterocycles: (a) Jain, S. L.; Sharma, V. B.; Sain, B. Tetrahedron Lett. 2003, 44, 4385.
25. (b) He, L.; Chan, P. W. H.; Tsui, W.-M.; Yu, W.-Y.; Che, C.-M. Org. Lett. 2004, 6, 2405.
26. Sulfides and sulfoxides: (a) Okamura, H.; Bolm, C. Org. Lett. 2004, 6, 1305.
27. (b) Mancheno, O. G.; Bolm, C. Org. Lett. 2006, 8, 2349.
28. (c) Muller, J. F. K.; Vogt, P. Tetrahedron Lett. 1998, 39, 4805.
29. (d) Takada, H.; Nishibayashi, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 1997, 62, 6512.
30. (e) Leca, D.; Song, K.; Amatore, M.; Fensterbank, L.; Lacote, E.; Malacria, M. Chem. Eur. J. 2004, 10, 906.
31. (f) Nishibayashi, Y.; Chiba, T.; Ohe, K.; Uemura, S. J. Chem. Soc., Chem. Commun. 1995, 1243.
32. Phosphines Yamada, Y.; Yamamoto, T.; Okawara, M. Chem. Lett. 1975, 361.
33. Arsines Ou, W.; Wang, Z.-G.; Chen, Z.-C. Synth. Commun. 1999, 29, 2301.
34. Ochiai, M.; Kaneaki, T.; Tada, N.; Miyamoto, K.; Chuman, H.; Shiro, M.; Hayashi, S.; Nakanishi, W. J. Am. Chem. Soc. 2007, 129, 12938.
35. For reviews on N-heterocyclic ammonium ylides, see: (a) Tamura, Y.; Ikeda, M. Adv. Heterocycl. Chem. 1981, 29, 71.
36. (b) Timpe, H.-J. Adv. Heterocycl. Chem. 1974, 17, 213.
37. The pyridinium ylide 2a has been prepared by thermal reaction (80 °C) of triflyl azide in pyridine in the presence of Cu catalyst in a moderate yield (47%). See: Xu, Y.; Zhu, S. Tetrahedron 1999, 55, 13725.
38. Ochiai, M.; Suefuji, T.; Miyamoto, K.; Shiro, M. Org. Lett. 2005, 7, 2893.
39. See Supporting Information, CCDC-705152 for 2c, and CCDC-705153 for 2k.
40. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1978, S1.
41. For solid-state structures of iminoammonium ylides, see: (a) Legault, C.; Charette, A. B. J. Am. Chem. Soc. 2003, 125, 6360.
42. (b) Poe, R.; Schnapp, K.; Young, M. J. T.; Grayzar, J.; Platz, M. S. J. Am. Chem. Soc. 1992, 114, 5054.
43. (c) Morris, D. G.; Muir, K. W.; Chii, C. O. W. Polyhedron 2003, 22, 3345.
44. (d) Cameron, A. F.; Duncanson, F. D.; Morris, D. G. Acta Crystallogr. 1976, B32, 1987.
45. 3-brornane 5, yielding directly the pyridinium ylide 2a, cannot be rigorously ruled out.
46. Ochiai, M.; Tada, N.; Okada, T.; Sota, A.; Miyamoto, K. J. Am. Chem. Soc. 2008, 130, 2118.
47. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
48. Addition of excess p-(trifluoromethyl)bromobenzene (0.5 M) did not decrease the rate of formation of 2h to a discernible extent.