A new and efficient method for the chemoselective reduction of azidoarenes and aroylazides: Use of zinc-cobalt chloride

Chemistry Letters

Volumn , Issue 8, 1997, Pages 789-790

  Baruah, Mukulesh ^a   Hussain, Akhtara ^a   Prajapati, Dipak ^a   Sandhu, Jagir S ^a  

^a REGIONAL RESEARCH LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031518943     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.789     Document Type: Article

References (23)

1. A recent review has updated the rich scope of azide chemistry and provided exhaustive coverage of methods for the reduction of azides to amines see: E. Sriven, K. Turnbull, Chem. Rev., 88, 297 (1988); C. Grundmann, in: Houbenweyl, Methoden der Organischen Chemie, 4th ed., E. Muller, (ed), Vol. 10/3, Georg Thieme Verlag. Stuttgart (1965), p. 822; T. Sheradsky, The Chemistry of the Azido Group, ed. by S. Patai, Interscience Publishers, London (1971), p. 333.
2. A recent review has updated the rich scope of azide chemistry and provided exhaustive coverage of methods for the reduction of azides to amines see: E. Sriven, K. Turnbull, Chem. Rev., 88, 297 (1988); C. Grundmann, in: Houbenweyl, Methoden der Organischen Chemie, 4th ed., E. Muller, (ed), Vol. 10/3, Georg Thieme Verlag. Stuttgart (1965), p. 822; T. Sheradsky, The Chemistry of the Azido Group, ed. by S. Patai, Interscience Publishers, London (1971), p. 333.
3. A recent review has updated the rich scope of azide chemistry and provided exhaustive coverage of methods for the reduction of azides to amines see: E. Sriven, K. Turnbull, Chem. Rev., 88, 297 (1988); C. Grundmann, in: Houbenweyl, Methoden der Organischen Chemie, 4th ed., E. Muller, (ed), Vol. 10/3, Georg Thieme Verlag. Stuttgart (1965), p. 822; T. Sheradsky, The Chemistry of the Azido Group, ed. by S. Patai, Interscience Publishers, London (1971), p. 333.
4. J. H. Boyer, J. Am. Chem. Soc., 73, 5865 (1951).
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7. For most recent reports using expensive samarium or samarium iodide see: Y. Huang, Y. Zhang, and Y. Wang, Tetrahedron Lett., 38, 1065 (1997); A. M. Salunkhe and H. C. Brown, Tetrahedron lett., 36, 7987 (1995); C. A. M. Afonso, Tetrahedron Lett., 36, 8857 (1995); L. Benati, P. C. Montevecchi, D. Nanni, P. Spagnolo, and M. Volta, Tetrahedron Lett., 36, 7313 (1995); Using Bakers' yeast see: M. Baruah, A. Boruah, D. Prajapati, and J. S. Sandhu, SynLett., 1996, 1193.
8. For most recent reports using expensive samarium or samarium iodide see: Y. Huang, Y. Zhang, and Y. Wang, Tetrahedron Lett., 38, 1065 (1997); A. M. Salunkhe and H. C. Brown, Tetrahedron lett., 36, 7987 (1995); C. A. M. Afonso, Tetrahedron Lett., 36, 8857 (1995); L. Benati, P. C. Montevecchi, D. Nanni, P. Spagnolo, and M. Volta, Tetrahedron Lett., 36, 7313 (1995); Using Bakers' yeast see: M. Baruah, A. Boruah, D. Prajapati, and J. S. Sandhu, SynLett., 1996, 1193.
9. For most recent reports using expensive samarium or samarium iodide see: Y. Huang, Y. Zhang, and Y. Wang, Tetrahedron Lett., 38, 1065 (1997); A. M. Salunkhe and H. C. Brown, Tetrahedron lett., 36, 7987 (1995); C. A. M. Afonso, Tetrahedron Lett., 36, 8857 (1995); L. Benati, P. C. Montevecchi, D. Nanni, P. Spagnolo, and M. Volta, Tetrahedron Lett., 36, 7313 (1995); Using Bakers' yeast see: M. Baruah, A. Boruah, D. Prajapati, and J. S. Sandhu, SynLett., 1996, 1193.
10. For most recent reports using expensive samarium or samarium iodide see: Y. Huang, Y. Zhang, and Y. Wang, Tetrahedron Lett., 38, 1065 (1997); A. M. Salunkhe and H. C. Brown, Tetrahedron lett., 36, 7987 (1995); C. A. M. Afonso, Tetrahedron Lett., 36, 8857 (1995); L. Benati, P. C. Montevecchi, D. Nanni, P. Spagnolo, and M. Volta, Tetrahedron Lett., 36, 7313 (1995); Using Bakers' yeast see: M. Baruah, A. Boruah, D. Prajapati, and J. S. Sandhu, SynLett., 1996, 1193.
11. For most recent reports using expensive samarium or samarium iodide see: Y. Huang, Y. Zhang, and Y. Wang, Tetrahedron Lett., 38, 1065 (1997); A. M. Salunkhe and H. C. Brown, Tetrahedron lett., 36, 7987 (1995); C. A. M. Afonso, Tetrahedron Lett., 36, 8857 (1995); L. Benati, P. C. Montevecchi, D. Nanni, P. Spagnolo, and M. Volta, Tetrahedron Lett., 36, 7313 (1995); Using Bakers' yeast see: M. Baruah, A. Boruah, D. Prajapati, and J. S. Sandhu, SynLett., 1996, 1193.
12. N. M. Yoom, J. Choi, and Y. S. Shon, Synth. Commun., 23, 3047 (1993).
13. S. G. Alverez, G. B. Fisher, and B. Singavam, Tetrahedron Lett., 36, 2567 (1995).
14. P. A. S. Smith, J. H. Hall, and R. O. Kan, J. Am. Chem. Soc., 84, 485 (1962); T. Gastiser, C. Selve, and J. J. Delpucch, Tetrahedron Lett., 24, 1609 (1983).
15. P. A. S. Smith, J. H. Hall, and R. O. Kan, J. Am. Chem. Soc., 84, 485 (1962); T. Gastiser, C. Selve, and J. J. Delpucch, Tetrahedron Lett., 24, 1609 (1983).
16. A. R. Ramesha, S. Bhat, and S. Chandresekan, J. Org. Chem., 60, 7682 (1995).
17. Cobalt chloride and zinc powder used were of commercial grade and procured from Central Drug House (Pvt.) Ltd., New Delhi-110002.
18. This reduction system was also used for the reduction of carbonyl compounds see: R. N. Baruah, Indian J. Chem., 33B, 182, (1994) and references cited therein.
19. R N. Baruah, Indian J. Chem. 33B, 758, (1994).
20. 3SnH/AlBN see: M. C. Samano and M. Robins, Tetrahedron Lett., 32, 6293 (1991); Using Ca/MeOH see: S. N. Maitti, P. Spevak, and A. V. N. Reddy, Synth. Commun., 18, 1201 (1988).
21. 3SnH/AlBN see: M. C. Samano and M. Robins, Tetrahedron Lett., 32, 6293 (1991); Using Ca/MeOH see: S. N. Maitti, P. Spevak, and A. V. N. Reddy, Synth. Commun., 18, 1201 (1988).
22. 3SnH/AlBN see: M. C. Samano and M. Robins, Tetrahedron Lett., 32, 6293 (1991); Using Ca/MeOH see: S. N. Maitti, P. Spevak, and A. V. N. Reddy, Synth. Commun., 18, 1201 (1988).
23. 3SnH/AlBN see: M. C. Samano and M. Robins, Tetrahedron Lett., 32, 6293 (1991); Using Ca/MeOH see: S. N. Maitti, P. Spevak, and A. V. N. Reddy, Synth. Commun., 18, 1201 (1988).