Sm°/Cat. I2 and SmI2 induced reductive coupling of nitriles with azides
Wei-Ke Su
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, China
Department of Chemistry, Zhejiang University at Xixi Campus, Hangzhou, Zhejiang 310028, China
Search for more papers by this authorYong-Shu Li
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, China
Search for more papers by this authorYong-Min Zhang
Department of Chemistry, Zhejiang University at Xixi Campus, Hangzhou, Zhejiang 310028, China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorWei-Ke Su
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, China
Department of Chemistry, Zhejiang University at Xixi Campus, Hangzhou, Zhejiang 310028, China
Search for more papers by this authorYong-Shu Li
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, China
Search for more papers by this authorYong-Min Zhang
Department of Chemistry, Zhejiang University at Xixi Campus, Hangzhou, Zhejiang 310028, China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorAbstract
The intermolecular reductive coupling of nitriles with azides induced by Sm°/Cat. I2 or SmI2 was studied. Aromatic and aliphatic amidines were prepared in moderate to good yields under neutral and mild conditions respectively.
References
- 1 For reviews see;. (a) Molander, G. A; Harris, C. R., Chem. Rev. 1996, 96, 307. (b) Molander, G. A., Org. React. 1994, 46, 221. (c) Imamoto, T., Larahanides in Organic Synthesis, Ace-deraic press, London, 1994. (d) Molander, G. A., Chem. Rev. 1992, 92, 29. (e) Yu, M. X; Zhang, Y. M; Bao, W. L., Chin. J. Chem. 1999, 17, 4.
- 2 Girard, P; Namy, J. L; Kagan, H. B., J. Am. Chem. Soc. 1980, 102, 2693.
- 3(a) Zhang, Y. M; Lin, R. H., Synth. Commun. 1987, 17, 329. (b) Souppe, J; Danon, L; Namy, J. L; Kagan, H. B., J. Organomet Chem. 1983, 250, 227.
- 4(a) Natale, N. R., Tetrahedron Lett. 1982, 23, 5009. (b) Benati, L; Monievecohi, P. C; Nanni, D. P; Spagnol, D; Volta, M., Tetrahedron Lett. 1995, 36, 7313. (c) Goulaouic-Dubois, C; Hesse, M., Tetrahedron Lett. 1995, 36, 7427.
- 5(a) Namy, J. L; Kagan, H. B., Tetrahedron Lett. 1983, 24, 765. (b) Molander, G. A; Etter, J. B; Hairing, L. S; Thorel, P. J., Am. Chem. Soc. 1991, 113, 8036.
- 6(a) Fukuzawa, S; Nalamishi, A; Fujinami, T; Sakai, S., J. Chem. Soc., Chem. Common. 1986, 624. (b) Fukuzawa, S; Nalamishi, A; Fujinami, T; Sakai, S., J. Chem. Soc., Perkin Trans 1 1988, 1669.
- 7(a) Jpatai, S; Rappoport, Z., The Chemistry of Amidines andlmidates, Vol. 27, Wiley & Son., New York, 1991, p. 226. (b) Kreutzberger, A., In Progress in Drug Research, Ed.: E. Jucker, Birklauser Verlag, Basel, 1968, p. 356.
- 8(a)
Lottermoser,
J. Praia. Chem.
1896,
54,
116.
10.1002/prac.18960540108 Google Scholar(b) Cooper, F. C; Partridge, M. W., J. Chem. Soc. 1953, 225. (c) Kalashnikpva, N. A; Kul'bitskii, G. N; Passet, B. V; Askinazi, B. Z., Zh. Org. Khim. 1974, 10, 1529.
- 9
Chen, J. X;
Chai, W. Y;
Zhu, J. L;
Gao, J;
Chen, W. X;
Kao, T. Y.,
Synthesis
1993,
1,
87.
10.1055/s-1993-25804 Google Scholar
- 10 Zhou, L. H; Zhang, Y. M., J. Chem. Soc., Perkin Trans 1. 1998, 2899.
- 11
Su, W. K;
Li, Y. S;
Zhang, Y. M.,
J. Chem. Research (S)
2001,
32.
10.3184/030823401103168190 Google Scholar
- 12 Gupta, K. A; Saxena, A. K; Jain, P. C; Srimal, R. C; Kar, K; Anand, N., Indian J. Chem. Sect. B. 1983, 22B, 384.
- 13 Gupta, K. A; Saxena, A. K; Dua, P. R; Srimal, R. C; Dhawan, B. N., Indian. IN 158 084, 1986. [Chem. Abstr. 1986, 107, P59051y].
