Bakers' Yeast Mediated Chemoselective Reduction of Azidoarenes

Synlett

Volumn 1996, Issue 12, 1996, Pages 1193-1194

  Baruah, Mukulesh ^a   Boruah, Anima ^a   Prajapati, Dipak ^a   Sandhu, Jagir S ^a  

^a REGIONAL RESEARCH LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542394627     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5710     Document Type: Article

References (20)

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2. Tsuboi, S.; Sakamoto, J.; Kawano, T.; Utaka, M.; Takeda, A., J. Org. Chem., 1991, 56, 7177 and references cited therein. Tsuboi, S.; Sakamoto, J.; Sakai, T.; Utaka, M., SynLett., 1991, 867.
3. For a recent review see : Csuk, R.; Glanzer, B. I., Chem. Rev., 1991, 91, 49. Servi, S., Synthesis, 1990, 1.
4. For a recent review see : Csuk, R.; Glanzer, B. I., Chem. Rev., 1991, 91, 49. Servi, S., Synthesis, 1990, 1.
5. Boyer, J. H., J. Am. Chem. Soc., 1951, 73, 5865.
6. Mungall, W. S.; Greene, G. L..; Heavner, G. A.; Letsinger, R. L., J. Org. Chem., 1975, 40, 1659.
7. Vaultier, M.; Knouzi, N.; Carrie, R., Tetrahedron Lett., 1983, 24, 763.
8. Koziara, A.; Pacewicka, K. O.; Zawadzki, S.; Zwierzak, A., Synthesis, 1985, 202.
9. Rolla, F., J. Org. Chem., 1982, 47, 4327.
10. Gastiser, T.; Selve, C.; Delpucch, J. J., Tetrahedron Lett., 1983, 24, 1609.
11. Suzuki, H.; Takaoka, K., Chem. Lett., 1984, 1733 and references cited therein.
12. For all of the work described here, we used bakers' yeast as supplied by Sigma.
13. For most recent reports see: Salunkhe, A. M.; Brown, H. C., Tetrahedron Lett., 1995, 36, 7987. Afonso, C. A. M., Tetrahedron Lett., 1995, 36, 8857. Benati, L.; Montevecchi, P. C.; Nanni, D.; Spagnolo, P.; Volta, M., Tetrahedron Lett., 1995, 36, 7313.
14. For most recent reports see: Salunkhe, A. M.; Brown, H. C., Tetrahedron Lett., 1995, 36, 7987. Afonso, C. A. M., Tetrahedron Lett., 1995, 36, 8857. Benati, L.; Montevecchi, P. C.; Nanni, D.; Spagnolo, P.; Volta, M., Tetrahedron Lett., 1995, 36, 7313.
15. For most recent reports see: Salunkhe, A. M.; Brown, H. C., Tetrahedron Lett., 1995, 36, 7987. Afonso, C. A. M., Tetrahedron Lett., 1995, 36, 8857. Benati, L.; Montevecchi, P. C.; Nanni, D.; Spagnolo, P.; Volta, M., Tetrahedron Lett., 1995, 36, 7313.
16. However excess use of bakers' yeast (250 g with 1 g of substrate) and long reaction time (around 100 hr) have impeded this reagent to employ as a good reducing agent in synthetic chemistry see: Takeshita, M.; Yoshida, S.; Kiya, R.; Hguchi, N.; Kobayashi, Y., Chem. Pharm. Bull., 1989, 37, 615.
17. Ehernkaufer, R.; Ram, S.; Tetrahedron Lett., 1984, 25, 3415. Heck, R. E.; Cortese, N. A., J. Org. Chem., 1977, 42, 3491.
18. Ehernkaufer, R.; Ram, S.; Tetrahedron Lett., 1984, 25, 3415. Heck, R. E.; Cortese, N. A., J. Org. Chem., 1977, 42, 3491.
19. Baik, W.; Han, J. L.; Lee, K. C.; Lee, N. H.; Kim, B. H.; Hahn, J. T., Tetrahedron Lett., 1994, 35, 3965.
20. Azide explodes in presence of metal catalysts see: Sanler, S. R., Organic Functional Group Preparation, Vol. II, Academic Press Inc. 1992, Chap. 13, p-325.