Reduction of azides to amines mediated by tin bis(1,2-benzenedithiolate)

Organic Letters

Volumn 2, Issue 3, 2000, Pages 397-399

  Bosch, Imma ^a   Costa, Anna M ^a   Martín, Manuel ^a   Urpí, Fèlix ^a   Vilarrasa, Jaume ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000979073     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991359z     Document Type: Article

References (48)

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29. II/PhSH complex in the field of natural products, see: Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693. Forrest, A. K.; O'Hanlon, P. J.; Walker, G. Tetrahedron 1994, 50, 19739. Kick, E. K.; Ellman, J. A. J. Med. Chem. 1995, 38, 1427. Urban, D.; Skrydstrup, T.; Riche, C.; Chiaroni, A.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1996, 1883. Lee, C. E.; Kick, E. K.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 9735. Urban, D.; Skrydstrup, T.; Beau, J.-M. J. Org. Chem. 1998, 63, 2507. Lee, J. W.; Fuchs, P. L. Org. Lett. 1999, 1, 179.
30. II/PhSH complex in the field of natural products, see: Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693. Forrest, A. K.; O'Hanlon, P. J.; Walker, G. Tetrahedron 1994, 50, 19739. Kick, E. K.; Ellman, J. A. J. Med. Chem. 1995, 38, 1427. Urban, D.; Skrydstrup, T.; Riche, C.; Chiaroni, A.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1996, 1883. Lee, C. E.; Kick, E. K.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 9735. Urban, D.; Skrydstrup, T.; Beau, J.-M. J. Org. Chem. 1998, 63, 2507. Lee, J. W.; Fuchs, P. L. Org. Lett. 1999, 1, 179.
31. II/PhSH complex in the field of natural products, see: Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693. Forrest, A. K.; O'Hanlon, P. J.; Walker, G. Tetrahedron 1994, 50, 19739. Kick, E. K.; Ellman, J. A. J. Med. Chem. 1995, 38, 1427. Urban, D.; Skrydstrup, T.; Riche, C.; Chiaroni, A.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1996, 1883. Lee, C. E.; Kick, E. K.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 9735. Urban, D.; Skrydstrup, T.; Beau, J.-M. J. Org. Chem. 1998, 63, 2507. Lee, J. W.; Fuchs, P. L. Org. Lett. 1999, 1, 179.
32. II/PhSH complex in the field of natural products, see: Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693. Forrest, A. K.; O'Hanlon, P. J.; Walker, G. Tetrahedron 1994, 50, 19739. Kick, E. K.; Ellman, J. A. J. Med. Chem. 1995, 38, 1427. Urban, D.; Skrydstrup, T.; Riche, C.; Chiaroni, A.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1996, 1883. Lee, C. E.; Kick, E. K.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 9735. Urban, D.; Skrydstrup, T.; Beau, J.-M. J. Org. Chem. 1998, 63, 2507. Lee, J. W.; Fuchs, P. L. Org. Lett. 1999, 1, 179.
33. II/PhSH complex in the field of natural products, see: Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693. Forrest, A. K.; O'Hanlon, P. J.; Walker, G. Tetrahedron 1994, 50, 19739. Kick, E. K.; Ellman, J. A. J. Med. Chem. 1995, 38, 1427. Urban, D.; Skrydstrup, T.; Riche, C.; Chiaroni, A.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1996, 1883. Lee, C. E.; Kick, E. K.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 9735. Urban, D.; Skrydstrup, T.; Beau, J.-M. J. Org. Chem. 1998, 63, 2507. Lee, J. W.; Fuchs, P. L. Org. Lett. 1999, 1, 179.
34. II/PhSH complex in the field of natural products, see: Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693. Forrest, A. K.; O'Hanlon, P. J.; Walker, G. Tetrahedron 1994, 50, 19739. Kick, E. K.; Ellman, J. A. J. Med. Chem. 1995, 38, 1427. Urban, D.; Skrydstrup, T.; Riche, C.; Chiaroni, A.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1996, 1883. Lee, C. E.; Kick, E. K.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 9735. Urban, D.; Skrydstrup, T.; Beau, J.-M. J. Org. Chem. 1998, 63, 2507. Lee, J. W.; Fuchs, P. L. Org. Lett. 1999, 1, 179.
35. II/PhSH complex in the field of natural products, see: Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693. Forrest, A. K.; O'Hanlon, P. J.; Walker, G. Tetrahedron 1994, 50, 19739. Kick, E. K.; Ellman, J. A. J. Med. Chem. 1995, 38, 1427. Urban, D.; Skrydstrup, T.; Riche, C.; Chiaroni, A.; Beau, J.-M. J. Chem. Soc., Chem. Commun. 1996, 1883. Lee, C. E.; Kick, E. K.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 9735. Urban, D.; Skrydstrup, T.; Beau, J.-M. J. Org. Chem. 1998, 63, 2507. Lee, J. W.; Fuchs, P. L. Org. Lett. 1999, 1, 179.
36. 4 combination shows, as expected, both dehydrating and reducing power. See: Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1990, 31, 7497.
37. These methods were developed in connection with a project on the direct macrolactamization of carboxyl-activated ω-azido acids, by reduction of the azido group and cyclization in situ, as we needed reagents chemoselective and strong enough for carrying out quickly the azido group reduction under the high-dilution conditions required for a successful macrocyclization. For applications to macrolactamization reactions, see: (a) Bartra, M.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1992, 33, 3669.
38. (b) Martín, M.; Mas, G.; Urpí, F.; Vilarrasa, J. Angew. Chem., Int. Ed. 1999, 38, 3086.
39. 6, 200 MHz) ° 6.82 (m, 2 H, AA′), 7.37 (m, 2 H, XX′).
40. For related tin dithiolates, see: (a) Epstein, L. M.; Straub, D. K. Inorg. Chem. 1965, 4, 1551.
41. (b) Poller, R. C.; Spillman, J. A. J. Chem. Soc. 1966, 958 and references therein.
42. (c) Sau, A. C.; Day, R. O.; Holmes, R. R. Inorg. Chem. 1981, 20, 3076.
43. (d) Sau, A. C.; Holmes, R. R.; Molloy, K. C.; Zuckerman, J. J. Inorg. Chem. 1982, 21, 1421.
44. Block, E.; Eswarakrishnan, V.; Gernon, M.; Ofon-Okai, G.; Saha, C.; Tang, K.; Zubieta, J. J. Am. Chem. Soc. 1989, 111, 658.
45. 3 (1.5 equiv): in THF at room temperature benzyl azide is reduced in 5 h.
46. 3, extraction several times with dichloromethane (or for the most polar compounds with ethyl acetate), drying of the organic extracts, filtration, and removal of the solvent under vacuum afforded a spectroscopically pure product. Filtration through a small pad of aluminum oxide or silica gel gave the chromatographically pure amine. By acidification of the aqueous layer up to ca. pH 2, a red solid (catalyst 1) precipitated; it was filtered off, dried, and reused when necessary.
47. The products are known compounds and have been characterized by NMR, IR, and MS.
48. 4 per millimole of benzyl azide, the complete disappearance of the azide required ca. 60 min (data not included in Table 1).