Selective allylation of arenethiols using water-soluble palladium complex catalyst in recyclable water/hexane biphasic media

Chemistry Letters

Volumn 34, Issue 2, 2005, Pages 246-247

  Komine, Nobuyuki ^a   Sako, Akari ^a   Hirahara, Shin Ya ^a   Hirano, Masafumi ^a   Komiya, Sanshiro ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALLYL COMPOUND; CARBON; HEXANE; PALLADIUM COMPLEX; THIOL DERIVATIVE; WATER;

ALLYLATION; AMBIENT AIR; ARTICLE; CATALYSIS; CATALYST; CULTURE MEDIUM; RECYCLING; SOLUBILITY; STEREOSPECIFICITY;

EID: 17844405288     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.246     Document Type: Article

References (29)

1. a) "Aqueous-Phase Organometallic Catalysis, Concepts and Applications," ed. by B. Cornils and W. A. Herrmann, Wiley-VCH, Weinheim (1998) and references cited therein,
2. b) "Applied Homogeneous Catalysis with Organometllic Compounds," ed. by B. Cornils and W. A. Herrmann, VCH, Weinheim (1996), Vols. 1 and 2.
3. a) S. Komiya, M. Ikuine, N. Komine, and M. Hirano, Chem. Lett., 2002, 72.
4. b) S. Komiya, M. Ikuine, N. Komine, and M. Hirano, Bull. Chem. Soc. Jpn., 76, 183 (2003).
5. A. Fukuoka, W. Kosugi, F. Morishita, M. Hirano, L. McCaffrey, W. Henderson, and S. Komiya, Chem. Commun., 1999, 489.
6. J. Tsuji, "Palladium Reagents and Catalysts," Wiley, Chichester (1995).
7. a) C. Goux, P. Lhoste, and D. Sinou, Tetrahedron Lett., 33, 8099 (1992).
8. b) M. Moreno-Mañas, R. Pleixats, and M. Villarroya, Tetrahedron, 49, 1457 (1993).
9. c) C. Goux, P. Lhoste, and D. Sinou, Tetrahedron, 50, 10321 (1994).
10. d) M. Frank and H.-J. Gais, Tetrahedron: Asymmetry, 9, 3353 (1998).
11. e) K. Tsutsumi, T. Yabukami, K. Fujimoto, T. Kawase, T. Morimoto, and K. Kakiuchi, Organometallics, 22, 2996 (2003).
12. T. Kondo, Y. Morisaki, S. Uenoyama, K. Wada, and T. Mitsudo, J. Am. Chem. Soc., 121, 8657 (1999).
13. A number of examples of the Tsuji-Trost reaction with allylic acetates or carbonates in water are known. a) M. Safi and D. Sinou, Tetrahedron Lett., 32, 2025 (1991). b) J. P. Genêt, E. Blart, and M. Savignac, Synlett, 1992, 715. c) E. Blart, J. P. Genêt, M. Safi, M. Savignac, and D. Sinou, Tetrahedron, 50, 505 (1994). d) D. E. Bergbreiter and Y.-S. Liu, Tetrahedron Lett., 38, 7843 (1997). e) H. Danjo, D. Tanaka, T. Hayashi, and Y. Uozumi, Tetrahedron, 55, 14341 (1999). f) S. Kobayashi, W. W.-L. Lam, and K. Manabe, Tetrahedron Lett., 41, 6115 (2000). g) Y. Uozumi and K. Shibatomi, J. Am. Chem. Soc., 123, 2919 (2001).
14. A number of examples of the Tsuji-Trost reaction with allylic acetates or carbonates in water are known. a) M. Safi and D. Sinou, Tetrahedron Lett., 32, 2025 (1991). b) J. P. Genêt, E. Blart, and M. Savignac, Synlett, 1992, 715. c) E. Blart, J. P. Genêt, M. Safi, M. Savignac, and D. Sinou, Tetrahedron, 50, 505 (1994). d) D. E. Bergbreiter and Y.-S. Liu, Tetrahedron Lett., 38, 7843 (1997). e) H. Danjo, D. Tanaka, T. Hayashi, and Y. Uozumi, Tetrahedron, 55, 14341 (1999). f) S. Kobayashi, W. W.-L. Lam, and K. Manabe, Tetrahedron Lett., 41, 6115 (2000). g) Y. Uozumi and K. Shibatomi, J. Am. Chem. Soc., 123, 2919 (2001).
15. A number of examples of the Tsuji-Trost reaction with allylic acetates or carbonates in water are known. a) M. Safi and D. Sinou, Tetrahedron Lett., 32, 2025 (1991). b) J. P. Genêt, E. Blart, and M. Savignac, Synlett, 1992, 715. c) E. Blart, J. P. Genêt, M. Safi, M. Savignac, and D. Sinou, Tetrahedron, 50, 505 (1994). d) D. E. Bergbreiter and Y.-S. Liu, Tetrahedron Lett., 38, 7843 (1997). e) H. Danjo, D. Tanaka, T. Hayashi, and Y. Uozumi, Tetrahedron, 55, 14341 (1999). f) S. Kobayashi, W. W.-L. Lam, and K. Manabe, Tetrahedron Lett., 41, 6115 (2000). g) Y. Uozumi and K. Shibatomi, J. Am. Chem. Soc., 123, 2919 (2001).
16. A number of examples of the Tsuji-Trost reaction with allylic acetates or carbonates in water are known. a) M. Safi and D. Sinou, Tetrahedron Lett., 32, 2025 (1991). b) J. P. Genêt, E. Blart, and M. Savignac, Synlett, 1992, 715. c) E. Blart, J. P. Genêt, M. Safi, M. Savignac, and D. Sinou, Tetrahedron, 50, 505 (1994). d) D. E. Bergbreiter and Y.-S. Liu, Tetrahedron Lett., 38, 7843 (1997). e) H. Danjo, D. Tanaka, T. Hayashi, and Y. Uozumi, Tetrahedron, 55, 14341 (1999). f) S. Kobayashi, W. W.-L. Lam, and K. Manabe, Tetrahedron Lett., 41, 6115 (2000). g) Y. Uozumi and K. Shibatomi, J. Am. Chem. Soc., 123, 2919 (2001).
17. A number of examples of the Tsuji-Trost reaction with allylic acetates or carbonates in water are known. a) M. Safi and D. Sinou, Tetrahedron Lett., 32, 2025 (1991). b) J. P. Genêt, E. Blart, and M. Savignac, Synlett, 1992, 715. c) E. Blart, J. P. Genêt, M. Safi, M. Savignac, and D. Sinou, Tetrahedron, 50, 505 (1994). d) D. E. Bergbreiter and Y.-S. Liu, Tetrahedron Lett., 38, 7843 (1997). e) H. Danjo, D. Tanaka, T. Hayashi, and Y. Uozumi, Tetrahedron, 55, 14341 (1999). f) S. Kobayashi, W. W.-L. Lam, and K. Manabe, Tetrahedron Lett., 41, 6115 (2000). g) Y. Uozumi and K. Shibatomi, J. Am. Chem. Soc., 123, 2919 (2001).
18. A number of examples of the Tsuji-Trost reaction with allylic acetates or carbonates in water are known. a) M. Safi and D. Sinou, Tetrahedron Lett., 32, 2025 (1991). b) J. P. Genêt, E. Blart, and M. Savignac, Synlett, 1992, 715. c) E. Blart, J. P. Genêt, M. Safi, M. Savignac, and D. Sinou, Tetrahedron, 50, 505 (1994). d) D. E. Bergbreiter and Y.-S. Liu, Tetrahedron Lett., 38, 7843 (1997). e) H. Danjo, D. Tanaka, T. Hayashi, and Y. Uozumi, Tetrahedron, 55, 14341 (1999). f) S. Kobayashi, W. W.-L. Lam, and K. Manabe, Tetrahedron Lett., 41, 6115 (2000). g) Y. Uozumi and K. Shibatomi, J. Am. Chem. Soc., 123, 2919 (2001).
19. A number of examples of the Tsuji-Trost reaction with allylic acetates or carbonates in water are known. a) M. Safi and D. Sinou, Tetrahedron Lett., 32, 2025 (1991). b) J. P. Genêt, E. Blart, and M. Savignac, Synlett, 1992, 715. c) E. Blart, J. P. Genêt, M. Safi, M. Savignac, and D. Sinou, Tetrahedron, 50, 505 (1994). d) D. E. Bergbreiter and Y.-S. Liu, Tetrahedron Lett., 38, 7843 (1997). e) H. Danjo, D. Tanaka, T. Hayashi, and Y. Uozumi, Tetrahedron, 55, 14341 (1999). f) S. Kobayashi, W. W.-L. Lam, and K. Manabe, Tetrahedron Lett., 41, 6115 (2000). g) Y. Uozumi and K. Shibatomi, J. Am. Chem. Soc., 123, 2919 (2001).
20. 3-allyl intermediate. H. Kinoshita, H. Shinokubo, and K. Oshima, Org. Lett., 6, 4085 (2004).
21. a) J. Qu, Y. Ishihara, T. Oe, and N. Nagato, Nippon Kagaku Kaishi, 1996, 250.
22. b) M. Sakamoto, I. Shimizu, and A. Yamamoto, Bull. Chem. Soc. Jpn., 69, 1065 (1996).
23. c) Y. Masuyama, M. Kagawa, and Y. Kurusu, Chem. Lett., 1995, 1121.
24. d) Y. Tamaru, Y. Horino, M. Araki, S. Tanaka, and M. Kimura, Tetrahedron Lett., 41, 5705 (2000).
25. e) M. Kimura, Y. Horino, R. Mukai, S. Tanaka, and Y. Tamaru, J. Am. Chem. Soc., 123, 10401 (2001).
26. f) S.-C. Yang and Y.-C. Tasai, Organometallics, 20, 763 (2001).
27. g) F. Ozawa, H. Okamoto, S. Kawagsi, S. Yamamoto, T. Minami, and M. Yoshifuji, J. Am. Chem. Soc., 124, 10968 (2002).
28. h) Y. Kayaki, T. Koda, and T. Ikariya, J. Org. Chem., 69, 2595 (2004).
29. i) K. Manabe and S. Kobayashi, Org. Lett., 5, 3241 (2004).