Green protocol for conjugate addition of thiols to α,β -unsaturated ketones using a [Bmim] PF6/H2O system

Journal of Organic Chemistry

Volumn 68, Issue 18, 2003, Pages 7098-7100

  Yadav, J S ^a   Reddy, B V S ^a   Baishya, Gakul ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

THIOLS;

CATALYSTS; ORGANIC ACIDS; REACTION KINETICS;

KETONES;

KETONE DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CATALYST; HYDROPHOBICITY; REACTION TIME;

EID: 0041837310     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034335l     Document Type: Article

References (25)

1. (a) Fluharty, A. L. In The Chemistry of the Thiol Group; Patai, S., Ed.; Wiely: New York, 1974; Part 2, p 589.
2. (b) Clark, J. H. Chem. Rev. 1980, 80, 429.
3. (c) Fujita, E.; Nagao, Y. J. Bioorg. Chem. 1977, 6 287.
4. (a) Trost, B. M.; Keeley, D. E. J. Org. Chem. 1975, 40, 2013.
5. (b) Shono, T.; Matsumura, Y.; Kashimura, S.; Hatanaka, K. J. Am. Chem. Soc. 1979, 101, 4752.
6. (c) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 12974.
7. (a) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc, 1998, 120, 4043.
8. (b) Suzuki, K.; Ikekawa, A.; Mukaiyama, T. Bull. Soc. Chem. Jpn. 1982, 55, 3277.
9. (c) Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 363.
10. (a) Zahouily, M.; Abrouki, Y.; Rayadh, A. Tetrahedron Lett. 2002, 43, 7729.
11. (b) Abrouki, Y.; Zahouily, M.; Rayadh, A.; Bahlaouan, B.; Sebti, S. Tetrahedron Lett. 2002, 43, 8951.
12. (a) Kanemasa, S.; Oderaotoshi, Y.; Wada, E. J. Am. Chem. Soc. 1999, 121, 8675.
13. (b) Bandini, M.; Cozzi, P. G.; Giacomini, M.; Melchiorre, P.; Selva, S.; Umani-Ronchi, A. J. Org. Chem. 2002, 67, 3700.
14. (c) Subbareddy, K.; Sudalai, A.; Benicewicz, B. C. Tetrahedron Lett. 2001, 42, 3791.
15. (a) McDaid, P.; Chen, Y.; Deng, Li. Angew. Chem., Int. Ed. 2002, 41, 338.
16. (b) Helder, R.; Arends, R.; Bolt, W.; Hiemstra, H.; Wynberg, H. Tetrahedron Lett. 1977, 2181.
17. (c) Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 417.
18. Ranu, B. C.; Dey, S. S.; Hajra, A. Tetrahedron 2003, 59, 2417.
19. Sheldon, R. A. Chirotechnologies, Industrial Synthesis of Optically Active Compounds; Dekker Publishing: New York, 1993.
20. Sheldon, R. J. Chem. Soc., Chem. Commun. 2001, 2399.
21. (a) Welton, T. Chem. Rev. 1999, 99, 2071.
22. (b) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772.
23. Gordon, C. M. Applied Catalysis A: General 2001, 222, 101.
24. Preparation of ionic liquids: (a) Park, S.; Kazlauskas, R. J. J. Org. Chem. 2001, 66, 8395. (b) Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217.
25. Preparation of ionic liquids: (a) Park, S.; Kazlauskas, R. J. J. Org. Chem. 2001, 66, 8395. (b) Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron 1996, 15, 1217.