Tetrabutylammonium Peroxydisulfate in Organic Synthesis. Part 8. An Efficient and Convenient Nickel-catalyzed Oxidation of Primary Amines to Nitriles with Tetrabutylammonium Peroxydisulfate

Abstract

A series of primary amines are oxidized to the corresponding nitriles in excellent yields with tetrabutylammonium peroxydisulfate catalyzed by nickel copper formate under basic aqueous conditions.

References

1. Part 7, F. E. Chen, J. D. Liu, H. Fu, Z. Z. Peng and L. Y. Shao, Synth. Commun., in press.
2. (a) K. Nakagawa and T. Tsuji, Chem. Pharm. Bull., 1963, 11, 296; (b) A. Stojiljkovic, V. Andrejevic and M. Lj. Mihailovi, Tetrahedron, 1967, 23, 721; (c) T. G. Clarke, N. A. Hampson, J. B. Lee, J. R. Morley and B. Scanlon, Tetrahedron Lett., 1968, 5685; (d) J. B. Lee, C. Parkjn and M. J. Shaw, Tetrahedron, 1973, 29, 751; (e) T. Kajimoto, H. Takahashi and J. Tsuji, J. Org. Chem., 1976, 41, 1389; (f) T. Kametani, K. Takahashi, T. Ohsawa and M. Ihara, Synthesis, 1977, 245; (g) U. Feldhues and H. J. Schafer, Synthesis, 1982, 145; (h) R. Tang, S. E. Diamond, N. Neary and F. Mares, J. Chem. Soc., Chem. Commun., 1978, 562; (i) S. Cenini, F. Porta and M. Pizzottio, J. Mol. Catal., 1982, 15, 297; (j) F. Porta, C. Grotti, S. Cenini and G. Palmisano, J. Mol. Catal., 1989, 50, 333; (k) G. Green, W. P. Griffith, D. M. Hollmshead, S. V. Ley and M. Schroder, J. Chem. Soc., Perkin Trans. 1, 1984, 681; (l) S. Yamazaki and Y. Yamazaki, Bull. Chem. Soc. Jpn., 1990, 63, 301; (m) P. Capdevielle, A. Lavigne and M. Maumy, Synthesis, 1989, 451.
3. (a) M. F. Semmelhack and C. R. Schmid, J. Am. Chem. Soc., 1983, 105, 6732; (b) K. K. Barnes and C. K. Mann, J. Org. Chem., 1967, 32, 1474; (c) N. A. Hampson, J. B. Lee and K. I. MacDonald, Electrochim Acta, 1972, 17, 921; (d) A. U. Blackham, S. Kurak and J. L. Palmer, J. Electrochem. Soc., 1975, 212, 1081; (e) U. Feldhues and H. J. Schafer, Synthesis, 1982, 145; (f) T. Shono, Y. Matsumura and K. Inoue, J. Am. Chem. Soc., 1984, 106, 6075.
4. (a) J. C. Jung, H. C. Chai and Y. H. Kim, Tetrahedron Lett., 1993, 34, 3581; (b) H. C. Choi and Y. H. Kim, Synth. Commun., 1994, 24, 2307; (c) F. E. Chen, J. S. Yang, H. Zhang, C. S. Guan and J. L. Wan, Synth. Commun., 1995, 25, 3163; (d) F. E. Chen, A. C. Liu, Q. J. Yan, M. X. Liu, D. M. Zhang and L. Y. Shao, Synth. Commun., 1999, 29, 1049; (e) F. E. Chen, J. L. Wan, C. S. Guan, J. S. Yang and H. Zhang, Synth. Commun., 1996, 26, 253.
5. H. M. Sampath Kumar, P. K. Mohanty, M. Suresh Kumar and J. S. Yadav, Synth. Commun., 1997, 27, 1327.
6. J. Correia, Synthesis, 1994, 1127.
7. H. M. Sampath Kumar, B. V. Subba Reddy, P. Tiyupathi Reddy and J. S. Yadav, Synthesis, 1999, 587.
8. A. Saednya, Synthesis, 1985, 184.
9. H. M. Meshram, Synthesis, 1992, 943.
10. B. Kokel, G. Menichi and M. Hubert-Habart, Synthesis, 1985, 201.