In Situ Oxidation-Imine Formation-Reduction Routes from Alcohols to Amines

Organic Letters

Volumn 3, Issue 11, 2001, Pages 1637-1639

  Blackburn, Leonie ^a   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

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ARTICLE;

EID: 0000186578     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015819b     Document Type: Article

References (19)

1. Related one-pot oxidation-reduction routes to amines can be achieved electrolytically or via transition metal mediated processes, although harsh conditions are required and functional group tolerance is limited. For leading references, see: Ohtani, B.; Nakagawa, K.; Nishimoto, S.; Kagiya, T. Chem. Lett. 1986, 1917-1920. Murahashi, S.; Kondo, K.; Hakata, T. Tetrahedron Lett. 1982, 23, 229-232.
2. Related one-pot oxidation-reduction routes to amines can be achieved electrolytically or via transition metal mediated processes, although harsh conditions are required and functional group tolerance is limited. For leading references, see: Ohtani, B.; Nakagawa, K.; Nishimoto, S.; Kagiya, T. Chem. Lett. 1986, 1917-1920. Murahashi, S.; Kondo, K.; Hakata, T. Tetrahedron Lett. 1982, 23, 229-232.
3. Tarasevich, V. A.; Kozlov, N. G. Russ. Chem. Rev. 1999, 68, 55-72, and references therein.
4. Ley, S. V.; Bolli, M. H.; Hinzen, B.; Gervois, A.-G.; Hall, B. J. J. Chem. Soc., Perkin Trans, 1 1998, 2239-2241. Ley, S. V.; Massi, A. J. Chem. Soc., Perkin Trans, 1 2000, 3645-3654.
5. Ley, S. V.; Bolli, M. H.; Hinzen, B.; Gervois, A.-G.; Hall, B. J. J. Chem. Soc., Perkin Trans, 1 1998, 2239-2241. Ley, S. V.; Massi, A. J. Chem. Soc., Perkin Trans, 1 2000, 3645-3654.
6. For reviews covering the preparation and utility of imines, see: Adams, J. P. J. Chem. Soc., Perkin. Trans. 1 2000, 125-139. Bloch, R. Chem. Rev. 1998, 98, 1407-1438.
7. For reviews covering the preparation and utility of imines, see: Adams, J. P. J. Chem. Soc., Perkin. Trans. 1 2000, 125-139. Bloch, R. Chem. Rev. 1998, 98, 1407-1438.
8. Wei, X.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 3815-3818. Blackburn, L.; Wei, X.; Taylor, R. J. K. Chem. Commun. 1999, 1337- 1338. Wei, X.; Taylor, R. J. K. J. Org. Chem. 2000, 65, 616-620.
9. Wei, X.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 3815-3818. Blackburn, L.; Wei, X.; Taylor, R. J. K. Chem. Commun. 1999, 1337-1338. Wei, X.; Taylor, R. J. K. J. Org. Chem. 2000, 65, 616-620.
10. Wei, X.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 3815-3818. Blackburn, L.; Wei, X.; Taylor, R. J. K. Chem. Commun. 1999, 1337- 1338. Wei, X.; Taylor, R. J. K. J. Org. Chem. 2000, 65, 616-620.
11. Isolated reports of this process have been published, see: Iwata, M. Bull. Chem. Soc. Jpn. 1981, 54, 2835-2836. Medvedeva, A. S.; Safronova, L. P.; Chichkareva, G. G.; Voronkov, M. G. Bull. Acad. Sci. USSR Div. Chem. Sci. 1976, 25, 107-110.
12. Isolated reports of this process have been published, see: Iwata, M. Bull. Chem. Soc. Jpn. 1981, 54, 2835-2836. Medvedeva, A. S.; Safronova, L. P.; Chichkareva, G. G.; Voronkov, M. G. Bull. Acad. Sci. USSR Div. Chem. Sci. 1976, 25, 107-110.
13. Juaristi, E.; Murer, P.; Seebach, D. Synthesis 1993, 1243-1246.
14. Johannsen, M.; Jorgensen, K. A. Chem Rev. 1998, 98, 1689-1708.
15. 3 was investigated but none of the amine was produced.
16. Hutchins, R. O.; Natale, N. R.; Taffer, I. M. Chem. Commun. 1978, 1088-1089. Commercially available from Novabiochem, catalog no. 01-64-0337, although the reagent prepared according to the literature procedure gave more consistent results.
17. Gilman, N. W. Chem. Commun. 1971, 733-734.
18. For other ways of utilizing potentially incompatible reagents, see: Gelman, F.; Blum, J.; Avnir, P. J. Am. Chem. Soc. 2000, 122, 11999-12000.
19. Cohen, B. J.; Kraus, M. A.; Patchornik, A. J. Am. Chem. Soc. 1977, 99, 4165-4167 and references therein.