Ruthenium-Catalyzed Oxidative Cyanation of Tertiary Amines with Hydrogen Peroxide and Sodium Cyanide†
Shun-Ichi Murahashi Prof. Dr.
Department of Chemistry, Graduate School of Engineering Science, Osaka University, 1–3 Machikaneyama, Toyonaka, Osaka 560-8531, Japan
Present address: Department of Applied Chemistry, Faculty of Engineering, Okayama University of Science, 1–1 Ridaicho, Okayama, Okayama 700-0005, Japan, Fax: (+81) 86-256-9513
Search for more papers by this authorNaruyoshi Komiya Dr.
Department of Chemistry, Graduate School of Engineering Science, Osaka University, 1–3 Machikaneyama, Toyonaka, Osaka 560-8531, Japan
Search for more papers by this authorHiroyuki Terai
Department of Chemistry, Graduate School of Engineering Science, Osaka University, 1–3 Machikaneyama, Toyonaka, Osaka 560-8531, Japan
Search for more papers by this authorShun-Ichi Murahashi Prof. Dr.
Department of Chemistry, Graduate School of Engineering Science, Osaka University, 1–3 Machikaneyama, Toyonaka, Osaka 560-8531, Japan
Present address: Department of Applied Chemistry, Faculty of Engineering, Okayama University of Science, 1–1 Ridaicho, Okayama, Okayama 700-0005, Japan, Fax: (+81) 86-256-9513
Search for more papers by this authorNaruyoshi Komiya Dr.
Department of Chemistry, Graduate School of Engineering Science, Osaka University, 1–3 Machikaneyama, Toyonaka, Osaka 560-8531, Japan
Search for more papers by this authorHiroyuki Terai
Department of Chemistry, Graduate School of Engineering Science, Osaka University, 1–3 Machikaneyama, Toyonaka, Osaka 560-8531, Japan
Search for more papers by this authorThis work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.
Graphical Abstract
Vielseitige Zwischenstufen zur Synthese von N-Aryl-α-aminosäuren und N,N-disubstituierten 1,2-Diaminen sind durch Ruthenium-katalysierte oxidative Cyanierung von tertiären Aminen zugänglich. Die Verwendung von Wasserstoffperoxid als Oxidationsmittel in Gegenwart von NaCN/AcOH oder HCN liefert die entsprechenden α-Aminonitrile (siehe Schema).
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References
- 1
- 1aS.-I. Murahashi,N. Komiya, Ruthenium in Organic Synthesis (Ed.: ), Wiley-VCH, Weinheim, 2004, pp. 53–93;
10.1002/3527603832.ch3 Google Scholar
- 1bS.-I. Murahashi,Y. Imada, Transition Metals for Organic Synthesis, Vol. 2 (Eds. ), Wiley-VCH, Weinheim, 1998, pp. 373–383;
- 1c Cytochrome P450, Structure, Mechanism and Biochemistry, 2nd ed. ), Plenum, New York, 1995;
- 1dC. Geoffrey, Introduction to Alkaloids, Wiley, New York, 1981.
- 2S.-I. Murahashi, Angew. Chem. 1995, 107, 2670;
10.1002/ange.19951072205 Google ScholarAngew. Chem. Int. Ed. Engl. 1995, 34, 2443.
- 3S.-I. Murahashi, T. Naota, K. Yonemura, J. Am. Chem. Soc. 1988, 110, 8256.
- 4
- 4aS.-I. Murahashi, T. Naota, T. Kuwabara, T. Saito, H. Kumobayashi, S. Akutagawa, J. Am. Chem. Soc. 1990, 112, 7820;
- 4bS.-I. Murahashi, T. Saito, T. Naota, H. Kumobayashi, S. Akutagawa, Tetrahedron Lett. 1991, 32, 5991.
- 5
- 5aS.-I. Murahashi, T. Hirano, T. Yano, J. Am. Chem. Soc. 1978, 100, 348;
- 5bS.-I. Murahashi, T. Watanabe, J. Am. Chem. Soc. 1979, 101, 7429.
- 6
- 6aG. Strukul, Catalytic Oxidations with Hydrogen Peroxide as Oxidant, Kluwer, Dordrecht 1992;
- 6bC. W. Jones, Application of Hydrogen Peroxide and Derivatives, Royal Society of Chemistry, Cambridge 1999;
10.1039/9781847550132 Google Scholar
- 6cI. W. C. E. Arends, R. A. Sheldon, M. Wallau, U. Schuchardt, Angew. Chem. 1997, 109, 1190;
10.1002/ange.19971091104 Google ScholarAngew. Chem. Int. Ed. Engl. 1997, 36, 1144;
- 6dC. C. Romano, F. E. Kühn, W. A. Herrmann, Chem. Rev. 1997, 97, 3197;
- 6eI. W. C. E. Arends, R. A. Sheldon, Top. Catal. 2002, 19, 133;
- 6fB. S. Lane, K. Burgess, Chem. Rev. 2003, 103, 2457;
- 6gR. Noyori, M. Aoki, K. Sato, Chem. Commun. 2003, 1977.
- 7Oxidation of alkenes:
- 7aK. Sato, M. Aoki, R. Noyori, Science 1998, 281, 1646;
- 7bK. Kamata, K. Yonehara, Y. Sumida, K. Yamaguchi, S. Hikichi, N. Mizuno, Science 2003, 300, 964;
- 7cY. Ishii, K. Yamawaki, T. Ura, H. Yamada, T. Yoshida, M. Ogawa, J. Org. Chem. 1988, 53, 3587;
- 7dR. Neumann, M. Gara, J. Am. Chem. Soc. 1995, 117, 5066;
- 7eD. E. De Vos, J. L. Meinershagen, T. Bein, Angew. Chem. 1996, 108, 2355;
10.1002/ange.19961081911 Google ScholarAngew. Chem. Int. Ed. Engl. 1996, 35, 2211;
- 7fP. Battioni, J. P. Renaud, J. F. Bartoli, M. Reina-Arfiles, M. Fort, D. Mansuy, J. Am. Chem. Soc. 1988, 110, 8462;
- 7gV. Venturello, E. Alneri, M. Ricci, J. Org. Chem. 1983, 48, 3831; oxidation of alcohols:
- 7hK. Sato, M. Aoki, J. Takagi, R. Noyori, J. Am. Chem. Soc. 1997, 119, 12386;
- 7iG. Barak, J. Dakka, Y. Sasson, J. Org. Chem. 1988, 53, 3553;
- 7jS. E. Jacobson, D. A. Muccigrosso, F. Mares, J. Org. Chem. 1979, 44, 921;
- 7kO. Bortoline, V. Cobnte, F. D. Furia, G. Modena, J. Org. Chem. 1986, 51, 2661;
- 7lR. Zennaro, F. Pinna, G. Strukul, H. Arzoumanian, J. Mol. Catal. 1991, 70, 269;
- 7mC. Venturello, M. Gambaro, J. Org. Chem. 1991, 56, 5924;
- 7nA. C. Dangel, W. P. Griffith, B. C. Parkin, J. Chem. Soc. Dalton Trans. 1993, 2683; oxidation of secondary amines:
- 7oH. Mitsui, S. Zenki, T. Shiota, S.-I. Murahashi, J. Chem. Soc. Chem. Commun. 1984, 874;
- 7pS.-I. Murahashi, H. Mitsui, T. Shiota, T. Tsuda, S. Watanabe, J. Org. Chem. 1990, 55, 1736;
- 7qS.-I. Murahashi, T. Shiota, Tetrahedron Lett. 1987, 28, 2383;
- 7rS.-I. Murahashi, T. Naota, N. Miyaguchi, T. Nakato, Tetrahedron Lett. 1992, 33, 6991; oxidation of alkanes:
- 7sD. H. R. Barton, D. Doller, Acc. Chem. Res. 1992, 25 504;
- 7tA. Sobkowiak,H.-C. Tung,D. T. Sawyer, Progress in Organic Chemistry, Vol. 40 (Ed. ), Wiley, New York, 1992, pp. 291–352;
- 7uA. S. Goldstein, R. H. Beer, R. S. Drago, J. Am. Chem. Soc. 1994, 116, 2424;
- 7vN. Mizuno, C. Nozaki, I. Kiyoto, M. Misono, J. Am. Chem. Soc. 1998, 120, 9267.
- 8For the copper-catalyzed alkynylation of tertiary amines with tBuOOH, see Z. Li, C.-J. Li, J. Am. Chem. Soc. 2004, 126, 11810.
- 9D. Enders, J. P. Shilvock, Chem. Soc. Rev. 2000, 29, 359.
- 10
- 10aS.-I. Murahashi, N. Komiya, H. Terai, T. Nakae, J. Am. Chem. Soc. 2003, 125, 15312;
- 10bM. North, Angew. Chem. 2004, 116, 4218;
10.1002/ange.200301750 Google ScholarAngew. Chem. Int. Ed. 2004, 43, 4126.
- 11
- 11aT. Shono, T. Toda, N. Oshino, J. Am. Chem. Soc. 1982, 104, 2639;
- 11bG. T. Miwa, W. A. Garland, B. J. Hodshon, A. Y. H. Lu, D. B. Northrop, J. Biol. Chem. 1980, 255, 6049;
- 11cG. T. Miwa, J. S. Walsh, G. L. Kedderis, P. F. Hollenberg, J. Biol. Chem. 1983, 258, 14445.
- 12
- 12aJ. A. Thompson, J. L. Holtzman, Drug Metab. Dispos. 1974, 2, 577;
- 12bD. C. Heimbrook, R. I. Murray, K. D. Egeberg, S. G. Sligar, M. W. Nee, T. C. Bruice, J. Am. Chem. Soc. 1984, 106, 1514.
- 13C. F. H. Allen, R. K. Kimball, Org. Synth. Coll. Vol. II 1943, p. 498.
- 14
- 14aN. Tanaka, T. Tamai, H. Mukaiyama, A. Hirabayashi, H. Muranaka, S. Akahane, H. Miyata, M. Akahane, J. Med. Chem. 2001, 44, 1436;
- 14bR. E. Webb, A. D. Johnston, J. Dent. Res. 1991, 70, 211.
- 15G. C. Barrett, Chemistry and Biochemistry of the Amino Acids (Ed.: ), Chapman and Hall, London, 1985, pp. 246–296.
10.1007/978-94-009-4832-7_8 Google Scholar
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