Samarium-induced iodine-catalyzed reduction of imines: Synthesis of amine derivatives

Tetrahedron Letters

Volumn 40, Issue 37, 1999, Pages 6731-6734

  Banik, Bimal K ^a   Zegrocka, Oliwia ^a   Banik, Indrani ^a   Hackfeld, Linda ^a   Becker, Frederick F ^a  

^a UNIVERSITY OF TEXAS   (United States)

Author keywords

Radical; Reduction; Samarium metal; Secondary amines

Indexed keywords

AMINE; AROMATIC AMINE; DIAMINE; IMINE; IODINE; MONOAMINE; SAMARIUM;

ARTICLE; CATALYSIS; MOLECULAR INTERACTION; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS;

EID: 0033543614     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01395-7     Document Type: Article

References (13)

1. For example, see: (a) Fujimori, K.; Yoshimoto, H.; Oae, S. Tetrahedron Lett. 1980, 21, 3385.
2. (b) Matsumura, Y.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1982, 23, 1932.
3. Lopez, R. M.; Fu, G. C. Tetrahedron 1997, 53, 16349.
4. Banik, B. K.; Mukhopadhyay, C.; Venkatraman, M. S.; Becker, F. F. Tetrahedron Lett. 1998, 39, 7243.
5. Becker, F. F.; Banik, B. K. Bioorg. Med. Chem. Lett. 1998, 8, 2877.
6. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
7. Huang, Y.; Zhang, Y.; Wang, Y. Tetrahedron Lett. 1997, 38, 1065.
8. Molander, G.; Wolfe, C. N. J. Org. Chem. 1998, 63, 9031. In this report, samarium diiodide was prepared by reacting samarium metal (1.1 equiv.) with iodine (1.0 equiv.).
9. Lu, L.; Chang, H.-Y.; Fang, J. M. J. Org. Chem. 1999, 64, 843. In this report samarium triiodide was prepared by reacting samarium metal (1 equiv.) with iodine (1.5 equiv.).
10. Reductive dimerization of the imines by samarium iodide was first reported by Enholm and his group. For example, see: Enholm, E. J.; Forbes, D. C.; Holub, D. P. Synth. Commun. 1990, 20, 981.
11. Salt-free samarium triflate has been used for the reductive dimerization of the imines. For example, see: Collin, J.; Giuseppone, N.; Machrouhi, F.; Namy, J.-L.; Nief, F. Tetrahedron Lett. 1999, 40, 3161.
12. Nickel iodide has been used for the effective dimerization of the imines. For example, see: Machrouhi, F.; Namy, J. L. Tetrahedron Lett. 1999, 40, 1315.
13. For a recent example, see: Zhang, W. C.; Li, C. J. J. Org. Chem. 1999, 64, 3230.