New synthetic method of diorganyl selenides: Palladium-catalyzed reaction of PhSeSnBu3 with aryl and alkyl halides

Organic Letters

Volumn 1, Issue 11, 1999, Pages 1725-1727

  Nishiyama, Yutaka ^a   Tokunaga, Keiji ^a   Sonoda, Noboru ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001169844     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990233z     Document Type: Article

References (33)

1. Krief, A.; Hevesi, L. In Organoselenium Chemistry, Vol. 1; Springer-Verlag: Berlin, 1988. Paulmier, C. In Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986. Patai, S.; Rappoport, Z. In The Chemistry of Organic Selenium and Tellurium Compounds, Vols. 1 and 2; 1986. Krief, A. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M., Eds.; Pergamon Press: Oxford, 1991; pp 85-192 and references therein.
2. Krief, A.; Hevesi, L. In Organoselenium Chemistry, Vol. 1; Springer-Verlag: Berlin, 1988. Paulmier, C. In Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986. Patai, S.; Rappoport, Z. In The Chemistry of Organic Selenium and Tellurium Compounds, Vols. 1 and 2; 1986. Krief, A. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M., Eds.; Pergamon Press: Oxford, 1991; pp 85-192 and references therein.
3. Krief, A.; Hevesi, L. In Organoselenium Chemistry, Vol. 1; Springer-Verlag: Berlin, 1988. Paulmier, C. In Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986. Patai, S.; Rappoport, Z. In The Chemistry of Organic Selenium and Tellurium Compounds, Vols. 1 and 2; 1986. Krief, A. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M., Eds.; Pergamon Press: Oxford, 1991; pp 85-192 and references therein.
4. Krief, A.; Hevesi, L. In Organoselenium Chemistry, Vol. 1; Springer-Verlag: Berlin, 1988. Paulmier, C. In Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986. Patai, S.; Rappoport, Z. In The Chemistry of Organic Selenium and Tellurium Compounds, Vols. 1 and 2; 1986. Krief, A. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M., Eds.; Pergamon Press: Oxford, 1991; pp 85-192 and references therein.
5. There are some reports on the palladium complex-catalyzed reaction of aryl and alkyl halides with organic heteroatom compounds having heteroatom-heteroatom bonds. (i) B-B: Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508.
6. (ii) Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Kato, T.; Nagai, Y. Angew. Chem. 1978, 90, 288. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715.
7. (ii) Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Kato, T.; Nagai, Y. Angew. Chem. 1978, 90, 288. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715.
8. (ii) Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Kato, T.; Nagai, Y. Angew. Chem. 1978, 90, 288. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715.
9. (ii) Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Kato, T.; Nagai, Y. Angew. Chem. 1978, 90, 288. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715.
10. (ii) Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Kato, T.; Nagai, Y. Angew. Chem. 1978, 90, 288. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715.
11. (ii) Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Kato, T.; Nagai, Y. Angew. Chem. 1978, 90, 288. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715.
12. (ii) Si-Si: Matsumoto, H.; Nagashima, S.; Yoshihiro, K.; Nagai, Y. J. Organomet. Chem. 1975, 85, C1. Matsumoto, H.; Yoshihiro, K.; Nagashima, S.; Watanabe, H.; Nagai, Y. J. Organomet. Chem. 1977, 128, 401. Matsumoto, H.; Nagashima, S.; Kato, T.; Nagai, Y. Angew. Chem. 1978, 90, 288. Faboru, C.; Griffiths, R. W.; Pidcock, A. J. Organomet. Chem. 1982, 225, 331. Nakano, T.; Takahashi, M.; Ashizawa, T.; Arai, T.; Seki, S.; Matsumoto, H.; Nagai, Y. Chem. Lett. 1982, 613. Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912. Hatanaka, Y. Hiyama, T. Tetrahdron Lett. 1987, 28, 4715.
13. (iii) Al-Si: Trost, B. M.; Yoshida, J. Tetrahedron Lett. 1983, 24, 4895.
14. (iv) Si-P: Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748.
15. (v) Si-Sn: Mori, M.; Kaneta, N.; Shibasaki, M. J. Org. Chem. 1991, 56, 3486.
16. (vi) S-Sn: Beletzkaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683.
17. (vi) S-Sn: Beletzkaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683.
18. (vi) S-Sn: Beletzkaya, I. P. J. Organomet. Chem. 1983, 250, 551. Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699. Juxiang, C.; Crisp, G. T. Synth. Commun. 1992, 22, 683.
19. (vii) Sn-Sn: Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
20. (vii) Sn-Sn: Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317. Kosugi, M.; Shimizu, K.; Ohtani, A.; Migita, T. Chem. Lett. 1981, 829.
21. Nishiyama, Y.; Aoyama, S.; Hamanaka, S. Phosphorus, Silicon, Sulfur 1993, 65, 1245. Nishiyama, Y.; Ohashi, H.; Itoh, K.; Sonoda, N. Chem. Lett. 1998, 159.
22. Nishiyama, Y.; Aoyama, S.; Hamanaka, S. Phosphorus, Silicon, Sulfur 1993, 65, 1245. Nishiyama, Y.; Ohashi, H.; Itoh, K.; Sonoda, N. Chem. Lett. 1998, 159.
23. 5 See: Shimada, K.; Okuse, S.; Takikawa, Y. Bull. Chem. Soc. Jpn. 1992, 65, 2848. Segi, M.; Kato, M.; Nakajima, T.; Suga, S. Tetrahedron Lett. 1991, 32, 7427. Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Synlett 1991, 105. Harpp, D. N.; Gingras, M. J. Am. Chem. Soc. 1988, 110, 7737. Steliou, K.; Mrani, M. J. Am. Chem. Soc. 1982, 104, 3104. Baudler, M.; Suchomel, H.; Fürstenberg, G.; Schings, U. Angew. Chem., Int. Ed. Engl. 1981, 20, 1044. Crosse, B. C.; Hutson, G. V. J. Chem. Soc. A 1967, 2014.
24. 5 See: Shimada, K.; Okuse, S.; Takikawa, Y. Bull. Chem. Soc. Jpn. 1992, 65, 2848. Segi, M.; Kato, M.; Nakajima, T.; Suga, S. Tetrahedron Lett. 1991, 32, 7427. Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Synlett 1991, 105. Harpp, D. N.; Gingras, M. J. Am. Chem. Soc. 1988, 110, 7737. Steliou, K.; Mrani, M. J. Am. Chem. Soc. 1982, 104, 3104. Baudler, M.; Suchomel, H.; Fürstenberg, G.; Schings, U. Angew. Chem., Int. Ed. Engl. 1981, 20, 1044. Crosse, B. C.; Hutson, G. V. J. Chem. Soc. A 1967, 2014.
25. 5 See: Shimada, K.; Okuse, S.; Takikawa, Y. Bull. Chem. Soc. Jpn. 1992, 65, 2848. Segi, M.; Kato, M.; Nakajima, T.; Suga, S. Tetrahedron Lett. 1991, 32, 7427. Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Synlett 1991, 105. Harpp, D. N.; Gingras, M. J. Am. Chem. Soc. 1988, 110, 7737. Steliou, K.; Mrani, M. J. Am. Chem. Soc. 1982, 104, 3104. Baudler, M.; Suchomel, H.; Fürstenberg, G.; Schings, U. Angew. Chem., Int. Ed. Engl. 1981, 20, 1044. Crosse, B. C.; Hutson, G. V. J. Chem. Soc. A 1967, 2014.
26. 5 See: Shimada, K.; Okuse, S.; Takikawa, Y. Bull. Chem. Soc. Jpn. 1992, 65, 2848. Segi, M.; Kato, M.; Nakajima, T.; Suga, S. Tetrahedron Lett. 1991, 32, 7427. Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Synlett 1991, 105. Harpp, D. N.; Gingras, M. J. Am. Chem. Soc. 1988, 110, 7737. Steliou, K.; Mrani, M. J. Am. Chem. Soc. 1982, 104, 3104. Baudler, M.; Suchomel, H.; Fürstenberg, G.; Schings, U. Angew. Chem., Int. Ed. Engl. 1981, 20, 1044. Crosse, B. C.; Hutson, G. V. J. Chem. Soc. A 1967, 2014.
27. 5 See: Shimada, K.; Okuse, S.; Takikawa, Y. Bull. Chem. Soc. Jpn. 1992, 65, 2848. Segi, M.; Kato, M.; Nakajima, T.; Suga, S. Tetrahedron Lett. 1991, 32, 7427. Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Synlett 1991, 105. Harpp, D. N.; Gingras, M. J. Am. Chem. Soc. 1988, 110, 7737. Steliou, K.; Mrani, M. J. Am. Chem. Soc. 1982, 104, 3104. Baudler, M.; Suchomel, H.; Fürstenberg, G.; Schings, U. Angew. Chem., Int. Ed. Engl. 1981, 20, 1044. Crosse, B. C.; Hutson, G. V. J. Chem. Soc. A 1967, 2014.
28. 5 See: Shimada, K.; Okuse, S.; Takikawa, Y. Bull. Chem. Soc. Jpn. 1992, 65, 2848. Segi, M.; Kato, M.; Nakajima, T.; Suga, S. Tetrahedron Lett. 1991, 32, 7427. Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Synlett 1991, 105. Harpp, D. N.; Gingras, M. J. Am. Chem. Soc. 1988, 110, 7737. Steliou, K.; Mrani, M. J. Am. Chem. Soc. 1982, 104, 3104. Baudler, M.; Suchomel, H.; Fürstenberg, G.; Schings, U. Angew. Chem., Int. Ed. Engl. 1981, 20, 1044. Crosse, B. C.; Hutson, G. V. J. Chem. Soc. A 1967, 2014.
29. 5 See: Shimada, K.; Okuse, S.; Takikawa, Y. Bull. Chem. Soc. Jpn. 1992, 65, 2848. Segi, M.; Kato, M.; Nakajima, T.; Suga, S. Tetrahedron Lett. 1991, 32, 7427. Segi, M.; Kojima, T.; Nakajima, T.; Suga, S. Synlett 1991, 105. Harpp, D. N.; Gingras, M. J. Am. Chem. Soc. 1988, 110, 7737. Steliou, K.; Mrani, M. J. Am. Chem. Soc. 1982, 104, 3104. Baudler, M.; Suchomel, H.; Fürstenberg, G.; Schings, U. Angew. Chem., Int. Ed. Engl. 1981, 20, 1044. Crosse, B. C.; Hutson, G. V. J. Chem. Soc. A 1967, 2014.
30. 298 = 98.2 ± 3 kcal/mol. See: Ho, K. C. M. In Thermodynamic Data for Inorganic Sulfides, Selenides, and Tellurides; Rechhood Press: England, 1974; p 594.
31. 7 From these results, we suggested that the oxidative addition of PhI to low-valent palladium species might be the key step to the success of this coupling reaction.
32. 2 in 83% isolated yield. See: Han, L.-B.; Shimada, S.; Tanaka, M. J. Am. Chem. Soc. 1997, 119, 8133.
33. Rossi has reported the synthesis of (E)-1-alkenyl phenyl sulfides by the palladium-catalyzed reaction of 1-alkenyl bromides with trialkylstannyl phenyl sulfide. In this paper, they proposed that the first step of this reaction was the generation of vinyl palladium bromide species by the reaction of 1-alkenyl bromides with low-valent palladium species. See: Carpita, A.; Rossi, R.; Scamuzzi, B. Tetrahedron Lett. 1989, 30, 2699.