First transition-metal complex catalyzed addition of organic disulfides to alkenes enables the rapid synthesis of vicinal-dithioethers

Journal of the American Chemical Society

Volumn 121, Issue 2, 1999, Pages 482-483

  Kondo, Teruyuki ^a   Uenoyama, Shin Ya ^a   Fujita, Ken Ichi ^a   Mitsudo, Take Aki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; DISULFIDE; METAL COMPLEX; ORGANIC DISULFIDE; SULFIDE; UNCLASSIFIED DRUG; VICINAL DITHIOETHER;

ARTICLE; CATALYSIS; CRYSTALLOGRAPHY; DISSOCIATION; ENANTIOMER; METAL BINDING; MOLECULAR MODEL; REACTION ANALYSIS; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 0033585518     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983497+     Document Type: Article

References (33)

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7. In contrast, the transition-metal complex catalyzed transformation of thiols and thioethers has been relatively well developed: (a) Okamura, H.; Miura, M.; Takei, H. Tetrahedron Lett. 1979, 43. (b) Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902. (c) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1992, 33, 8099. (d) Bäckvall, J.-E.; Ericsson, A. J. Org. Chem. 1994, 59, 5850. (e) Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380 and references therein. (f) Xiao, W.-J.; Vasapollo, G.; Alper, H. J. Org. Chem. 1998, 63, 2609 and references therein.
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9. In contrast, the transition-metal complex catalyzed transformation of thiols and thioethers has been relatively well developed: (a) Okamura, H.; Miura, M.; Takei, H. Tetrahedron Lett. 1979, 43. (b) Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902. (c) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1992, 33, 8099. (d) Bäckvall, J.-E.; Ericsson, A. J. Org. Chem. 1994, 59, 5850. (e) Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380 and references therein. (f) Xiao, W.-J.; Vasapollo, G.; Alper, H. J. Org. Chem. 1998, 63, 2609 and references therein.
10. In contrast, the transition-metal complex catalyzed transformation of thiols and thioethers has been relatively well developed: (a) Okamura, H.; Miura, M.; Takei, H. Tetrahedron Lett. 1979, 43. (b) Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902. (c) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1992, 33, 8099. (d) Bäckvall, J.-E.; Ericsson, A. J. Org. Chem. 1994, 59, 5850. (e) Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380 and references therein. (f) Xiao, W.-J.; Vasapollo, G.; Alper, H. J. Org. Chem. 1998, 63, 2609 and references therein.
11. In contrast, the transition-metal complex catalyzed transformation of thiols and thioethers has been relatively well developed: (a) Okamura, H.; Miura, M.; Takei, H. Tetrahedron Lett. 1979, 43. (b) Kuniyasu, H.; Ogawa, A.; Sato, K.-I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902. (c) Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1992, 33, 8099. (d) Bäckvall, J.-E.; Ericsson, A. J. Org. Chem. 1994, 59, 5850. (e) Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380 and references therein. (f) Xiao, W.-J.; Vasapollo, G.; Alper, H. J. Org. Chem. 1998, 63, 2609 and references therein.
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24. For carbonylation, see: (a) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. For C-C bond formation, see: (b) Kondo, T.; Hiraishi, N.; Morisaki, Y.; Wada, K.; Watanabe, Y.; Mitsudo, T. Organometallics 1998, 17, 2131 and references therein. For C-C bond activation, see: (c) Kondo, T.; Kodoi, K.; Nishinaga, E.; Okada, T.; Morisaki, Y.; Watanabe, Y.; Mitsudo, T. J. Am. Chem. Soc. 1998, 120, 5587.
25. For carbonylation, see: (a) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. For C-C bond formation, see: (b) Kondo, T.; Hiraishi, N.; Morisaki, Y.; Wada, K.; Watanabe, Y.; Mitsudo, T. Organometallics 1998, 17, 2131 and references therein. For C-C bond activation, see: (c) Kondo, T.; Kodoi, K.; Nishinaga, E.; Okada, T.; Morisaki, Y.; Watanabe, Y.; Mitsudo, T. J. Am. Chem. Soc. 1998, 120, 5587.
26. For carbonylation, see: (a) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. For C-C bond formation, see: (b) Kondo, T.; Hiraishi, N.; Morisaki, Y.; Wada, K.; Watanabe, Y.; Mitsudo, T. Organometallics 1998, 17, 2131 and references therein. For C-C bond activation, see: (c) Kondo, T.; Kodoi, K.; Nishinaga, E.; Okada, T.; Morisaki, Y.; Watanabe, Y.; Mitsudo, T. J. Am. Chem. Soc. 1998, 120, 5587.
27. 2 (1a) with an equimolar amount of 2-norbornene (2a) reduced both the conversion of (1a) and the yield of adduct (3a) to 82% and 78%, respectively.
28. -1, Rigaku AFC7R diffractometer, 3667 reflections (unique), R = 0.043, wR = 0.046, GOF = 1.04.
29. 4 has already been reported: Matsuzaka, H.; Qu, J.-P.; Ogino, T.; Nishio, M.; Nishibayashi, Y., Ishii, Y.; Uemura, S.; Hidai, M. J. Chem. Soc., Dalton 1996, 4307.
30. Mitsudo, T.; Naruse, H.; Kondo, T.; Ozaki, Y.; Watanabe, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 580.
31. Inagaki, S.; Fujimoto, H.; Fukui, K. J. Am. Chem. Soc. 1976, 98, 4054.
32. The thioselenation of 2-norbornene under radical conditions gave a mixture of exo- and endo-adducts (ref 8). Therefore, the radical mechanism can be completely ruled out.
33. Metzner, P.; Thuillier, A. In Sulfur Reagents in Organic Synthesis; Academic Press: London, U.K., 1994; p. 75.