Palladium(II) acetate in pyridine as an effective catalyst for highly regioselective hydroselenation of alkynes

Journal of Organic Chemistry

Volumn 70, Issue 2, 2005, Pages 696-698

  Kamiya, Ikuyo ^a   Nishinaka, Etsuyo ^a   Ogawa, Akiya ^b  

^a NARA WOMEN'S UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CATALYSTS; OLEFINS; PALLADIUM COMPOUNDS;

BENZENESELENOL; HYDROSELENATION; PALLADIUM(II) ACETATE; PYRIDINE;

NITROGEN COMPOUNDS;

1 PHENYLSELENO 1 ALKENE; 2 PHENYLSELENO 1 ALKENE; 2,2' BIPYRIDINE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; BENZENE DERIVATIVE; BENZENESELENOL; PALLADIUM ACETATE; PYRIDINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL MODIFICATION; HYDROSELENATION;

EID: 12344312905     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048727j     Document Type: Article

References (35)

1. Reviews: (a) Ogawa, A. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 15. (b) Alonso, F.; Beletskaya, I.; Yus, M. Chem. Rev. 2004, 104, 3079. (c) Ogawa, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002; Chapter VII.6. (d) Kuniyasu, H. In Catalytic Heterofunctionalization; Togni, A., Grützmacher, H., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Chapter 7. (e) Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205. (f) Ogawa, A. J. Organomet. Chem. 2000, 611, 463. (g) Beletskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435. (h) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
2. Reviews: (a) Ogawa, A. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 15. (b) Alonso, F.; Beletskaya, I.; Yus, M. Chem. Rev. 2004, 104, 3079. (c) Ogawa, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002; Chapter VII.6. (d) Kuniyasu, H. In Catalytic Heterofunctionalization; Togni, A., Grützmacher, H., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Chapter 7. (e) Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205. (f) Ogawa, A. J. Organomet. Chem. 2000, 611, 463. (g) Beletskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435. (h) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
3. Reviews: (a) Ogawa, A. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 15. (b) Alonso, F.; Beletskaya, I.; Yus, M. Chem. Rev. 2004, 104, 3079. (c) Ogawa, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002; Chapter VII.6. (d) Kuniyasu, H. In Catalytic Heterofunctionalization; Togni, A., Grützmacher, H., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Chapter 7. (e) Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205. (f) Ogawa, A. J. Organomet. Chem. 2000, 611, 463. (g) Beletskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435. (h) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
4. Reviews: (a) Ogawa, A. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 15. (b) Alonso, F.; Beletskaya, I.; Yus, M. Chem. Rev. 2004, 104, 3079. (c) Ogawa, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002; Chapter VII.6. (d) Kuniyasu, H. In Catalytic Heterofunctionalization; Togni, A., Grützmacher, H., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Chapter 7. (e) Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205. (f) Ogawa, A. J. Organomet. Chem. 2000, 611, 463. (g) Beletskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435. (h) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
5. Reviews: (a) Ogawa, A. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 15. (b) Alonso, F.; Beletskaya, I.; Yus, M. Chem. Rev. 2004, 104, 3079. (c) Ogawa, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002; Chapter VII.6. (d) Kuniyasu, H. In Catalytic Heterofunctionalization; Togni, A., Grützmacher, H., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Chapter 7. (e) Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205. (f) Ogawa, A. J. Organomet. Chem. 2000, 611, 463. (g) Beletskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435. (h) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
6. Reviews: (a) Ogawa, A. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 15. (b) Alonso, F.; Beletskaya, I.; Yus, M. Chem. Rev. 2004, 104, 3079. (c) Ogawa, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002; Chapter VII.6. (d) Kuniyasu, H. In Catalytic Heterofunctionalization; Togni, A., Grützmacher, H., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Chapter 7. (e) Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205. (f) Ogawa, A. J. Organomet. Chem. 2000, 611, 463. (g) Beletskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435. (h) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
7. Reviews: (a) Ogawa, A. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 15. (b) Alonso, F.; Beletskaya, I.; Yus, M. Chem. Rev. 2004, 104, 3079. (c) Ogawa, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002; Chapter VII.6. (d) Kuniyasu, H. In Catalytic Heterofunctionalization; Togni, A., Grützmacher, H., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Chapter 7. (e) Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205. (f) Ogawa, A. J. Organomet. Chem. 2000, 611, 463. (g) Beletskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435. (h) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
8. Reviews: (a) Ogawa, A. In Main Group Metals in Organic Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 15. (b) Alonso, F.; Beletskaya, I.; Yus, M. Chem. Rev. 2004, 104, 3079. (c) Ogawa, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002; Chapter VII.6. (d) Kuniyasu, H. In Catalytic Heterofunctionalization; Togni, A., Grützmacher, H., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Chapter 7. (e) Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205. (f) Ogawa, A. J. Organomet. Chem. 2000, 611, 463. (g) Beletskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435. (h) Han, L.-B.; Tanaka, M. Chem. Commun. 1999, 395.
9. (a) Okamura, H.; Miura, M.; Kosugi, K.; Takei, H. Tetrahedron Lett. 1980, 21, 87.
10. (b) Murahashi, S.; Yano, T. J. Am. Chem. Soc. 1980, 102, 2456.
11. (c) Uemura, S.; Fukuzawa, S.; Patil, S. R. J. Organomet. Chem. 1983, 243, 9.
12. (d) Cristau, H. J.; Chabaud, B.; Labaudiniere, R.; Chistol, H. J. Org. Chem. 1986, 51, 875.
13. (e) Ohe, K.; Takahashi, H.; Uemura, S.; Sugita, N. J. Organomet. Chem. 1987, 326, 35.
14. (f) Takahashi, H.; Ohe, K.; Uemura, S.; Sugita, N. J. Organomet. Chem. 1987, 334, C43.
15. (g) Ohe, K.; Takahashi, H.; Uemura, S.; Sugita, N. J. Org. Chem. 1987, 52, 4859.
16. (h) Tsumuraya, T.; Ando, W. Organometallics 1989, 8, 2286.
17. (i) Fukuzawa, S.; Fujinami, T.; Sasai, S. Chem. Lett. 1990, 927.
18. (j) Kuniyasu, H.; Ogawa, A.; Miyazaki, S.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 9796.
19. (k) Uemura, S.; Takahashi, H.; Ohe, K. J. Organomet. Chem 1992, 423, C9.
20. (l) Kuniyasu, H.; Ogawa, A.; Higaki, K.; Sonoda, N. Organometallics 1992, 11, 3937.
21. (m) Kuniyasu, H.; Ogawa, A.; Sato, K.; Ryu, I.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525.
22. (n) Ogawa, A.; Sonoda, N. J. Synth. Org. Chem. Jpn. 1993, 51, 815.
23. (o) Han, L.-B.; Choi, N.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 7000.
24. (p) Ogawa, A.; Kuniyasu, H.; Sonoda, N.; Hirao, T. J. Org. Chem. 1997, 62, 8361.
25. (q) Kuniyasu, H.; Maruyama, A.; Kurosawa, H. Organometallics 1998, 17, 908.
26. (r) Ogawa, A.; Kuniyasu, H.; Takeba, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Organomet. Chem. 1998, 564, 1.
27. (s) Ogawa, A.; Kudo, A.; Hirao, T. Tetrahedron Lett. 1998, 39, 5213.
28. (t) Nishiyama, Y.; Tokunaga, K.; Sonoda, N. Org. Lett. 1999, 1, 1725.
29. Kuniyasu, H.; Ogawa, A.; Sato, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902.
30. Although the reason 2-phenyl-2-propenols were formed as byproducts in the case of propargylic alcohols is unclear, the coordination of the propargylic oxygen to palladium may contribute to the formation of the regioisomers (2-phenylseleno-2-propenol).
31. Ogawa, A.; Obayashi, R.; Sekiguchi, M.; Masawaki, T.; Kambe, N.; Sonoda, N. Tetrahedron Lett. 1992, 33, 1329.
32. 2) molecules as key species for this hydroselenation of alkynes easily react with each other by the coordination of the selenide ligand to the other palladium center to form polymerized complex, which is insoluble in usual organic solvents and loses the catalytic activation. Therefore, pyridine might inhibit the polymerization and protect the catalyst from the poisoning.
33. (a) Ananikov, V. P.; Beletskaya, I. P.; Aleksandrov, G. G.; Eremenko, I. L. Organometallics 2003, 22, 1414.
34. (b) Ananikov, V. P.; Malyshev, D. A.; Beletskaya, I. P.; Aleksandrov G. G.; Eremenko, I. L. J. Organomet. Chem. 2003, 679, 162.
35. (c) Ananikov, V. P.; Malyshev, D. A.; Beletskaya, I. P.; Aleksandrov G. G.; Eremenko, I. L. J. Organomet. Chem. 2003, 687, 451.