Catalytic Lewis acid activation of thionyl chloride: Application to the synthesis of aryl sulfinyl chlorides catalyzed by bismuth(III) salts

Synlett

Volumn , Issue 5, 2003, Pages 631-634

  Peyronneau, Magali ^a   Roques, Nicolas ^b   Mazières, Stéphane ^a   Le Roux, Christophe ^a  

^a UMR 5069) 118 route de Narbonne   (France)

^b Rhodia Europe   (France)

Author keywords

Bismuth reagents; Catalysis; Electrophilic activation; Friedel Crafts reactions; Thionyl chloride

Indexed keywords

ANISOLE; BISMUTH SALT; CHLORIDE; LEWIS ACID; THIONYL CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRODUCTIVITY; SYNTHESIS;

EID: 0037265106     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (32)

1. Oka, K. Synthesis 1981, 661.
2. Olah, G. A.; Marinez, E. R.; Prakash, G. K. S. Synlett 1999, 1397.
3. (a) Olah, G. A.; Nishimura, J. J. Org. Chem. 1974, 39, 1203.
4. (b) Fujisawa, T.; Kakutani, M.; Kobayashi, N. Bull. Soc. Chem. Jpn. 1973, 46, 3615.
5. (a) Schubart, R. In Ullmann's Encyclopedia of Industrial Chemistry, Vol. A25; Gerhartz, W., Ed.; VCH: Weinheim, 1985, 461-476; and references cited.
6. (b) Schwan, A. L.; Strickler, R. R. Org. Prep. Proced. Int. 1999, 31, 579.
7. (a) Douglass, I. B.; Norton, R. V. J. Org. Chem. 1968, 33, 2104.
8. (b) Kee, M. L.; Douglass, I. B. Org. Prep. Proced. 1970, 2, 235.
9. Douglass, I. B.; Farah, B. S.; Thomas, E. G. J. Org. Chem. 1961, 26, 1996.
10. (a) Bell, K. H. Aust. J. Chem. 1985, 38, 1209.
11. (b) Bell, K. H.; McCaffery, L. F. Aust. J. Chem. 1992, 45, 1213.
12. (a) Karade, N. N.; Kate, S. S.; Adude, R. N. Synlett 2001, 1573.
13. 7a
14. 8a.
15. (a) Labrouillère, M.; Le Roux, C.; Gaspard-Iloughmane, H.; Dubac, J. Syntett 1994, 723.
16. (b) Labrouillère, M.; Le Roux, C.; Gaspard-Iloughmane, H.; Dubac, J. Bull. Soc. Chim. Fr. 1995, 132, 522.
17. For a review about Friedel-Crafts and related reactions catalyzed by 2 or 3 see: Le Roux, C.; Dubac, J. Synlett 2002, 181.
18. (a) Desmurs, J. R.; Labrouillère, M.; Dubac, J.; Laporterie, A.; Gaspard, H.; Metz, F. Ind. Chem. Libr. 1996, 8.
19. (b) The Roots of Organic Development; Desmurs, J.-R.; Ratton, S., Eds.; Elsevier: Amsterdam, 1996, 15-28.
20. (c) Desmurs, J. R.; Labrouillère, M.; Le Roux, C.; Gaspard, H.; Laporterie, A.; Dubac, J. Tetrahedron Lett. 1997, 38, 8871.
21. (d) Répichet, S.; Le Roux, C.; Dubac, J.; Desmurs, J. R. Eur. J. Org. Chem. 1998, 2743.
22. Répichet, S.; Le Roux, C.; Hernandez, P.; Dubac, J.; Desmurs, J. R. J. Org. Chem. 1999, 64, 6479.
23. Suzuki, H.; Matano, Y. Organobismuth Chemistry; Elsevier: Amsterdam, 2001, Chap. 1, 1-20.
24. (a) Répichet, S.; Zwick, A.; Vendier, L.; Le Roux, C.; Dubac, J. Tetrahedron Lett. 2002, 43, 993.
25. (b) Another method of preparation of 3 has been previously reported: Labrouillère, M.; LeRoux, C.; Gaspard, H.; Laporterie, A.; Dubac, J.; Desmurs, J. R. Tetrahedron Lett. 1999, 40, 285.
26. Kobayashi, S.; Komoto, I. Tetrahedron 2000, 56, 6463.
27. Douglass, I. B.; Koop, D. A. J. Org. Chem. 1964, 29, 951.
28. From our experience the stability of aryl sulfinyl chlorides seems highly unpredictable.
29. 19F NMR in the recovered 1.
30. 1H NMR signals of 4 remained unchanged.
31. (a) Yadav, J. S.; Subba Reddy, B. V.; Srinivasa Rao, R.; Praveen Kumar, S.; Nagaiah, K. Synlett 2002, 784.
32. abstract