Expedient synthesis of sulfinamides from sulfonyl chlorides

Journal of Organic Chemistry

Volumn 72, Issue 2, 2007, Pages 683-685

  Harmata, Michael ^a   Zheng, Pinguan ^a   Huang, Chaofeng ^a   Gomes, Maria G ^a   Ying, Weijiang ^a   Ranyanil, Kanok On ^a   Balan, Gayatri ^a   Calkins, Nathan L ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE COMPOUNDS; IN SITU PROCESSING; REACTION KINETICS; SYNTHESIS (CHEMICAL);

IN SITU REDUCTION; SULFINAMIDES; SULFONYL CHLORIDES;

NITROGEN COMPOUNDS;

ACETONITRILE; ALKENE; ALKYNE; BENZOTHIAZINE DERIVATIVE; CHLORIDE; HYPOCHLORITE; SULFINAMIDE; SULFUR DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE; TRIETHYLAMINE; TRIPHENYLPHOSPHINE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; OXIDATION; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE;

AMIDES; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFINIC ACIDS; SULFUR COMPOUNDS;

EID: 33846243877     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062296i     Document Type: Article

References (29)

1. (a) Ellman, J. A. Pure Appl. Chem. 2003, 75, 39.
2. (b) Senanayake, C. H.; Krishnamurthy, D.; Lu, Z.-H.; Han, Z.; Gallor, I. Aldrichim. Acta 2005, 38, 93.
3. (a) Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772.
4. (b) Hannam, J.; Harrison, T.; Heath, F.; Madin, A.; Merchant, K. Synlett 2006, 833.
5. (c) Kells, K. W.; Chong. J. M. Org. Lett. 2003, 5, 4215.
6. Furukawa, M.; Okawara, T. Synthesis 1976, 339.
7. (a) Billard, T.; Greiner, A.; Langlois, B. R. Tetrahedron 1999, 55, 7243.
8. (b) Davis, F. A.; Zhang, Y.; Andemichael, Y.; Fang, T.; Fanelli, D. L.; Zhang, H. J. Org. Chem. 1999, 64, 1403.
9. (c) Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555.
10. (d) Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, 8003.
11. Uchino, M.; Sekiya, M. Chem. Pharm. Bull. 1980, 28, 126.
12. Cogan, D. A.; Liu, G.; Kim, K.; Backes, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 8011.
13. Coulomb, J.; Certal, V.; Fensterbank, L.; Lacôte, E.; Malacria, M. Angew. Chem., Int. Ed. 2006, 45, 633.
14. Tillet, J. G. Sulfinamides. In The Chemistry of Sulphinic Acids, Esters and their Derivatives; Patai, S., Ed.: Wiley: Chicheter, 1990; pp 603-22.
15. For examples, see: (a) Reggelin, M.; Junker, B. Chem. Eur. J. 2001, 7, 1232.
16. (b) Furusho, Y.; Okada, Y.; Takata, T. Bull. Soc. Chem. Jpn. 2000, 73, 2827.
17. (c) Roy, A. K. J. Am. Chem. Soc. 1993, 115, 2598.
18. (d) Kim, Y. H.; Yoon, D. C. Synth. Commun. 1989, 19, 1569.
19. (e) Johnson, C. R.; Bis, K. G.; Cantillo, J. H.; Meanwell, N. A.; Reinhard, M. F. D.; Zeller, J. R.; Vonk, G. P. J. Org. Chem. 1983, 48, 1.
20. (a) Harmata, M.; Schlemper, E. O. Tetrahedron Lett. 1987, 28, 5997.
21. (b) Harmata, M.; Claassen, R. J., II; Barnes, C. L. J. Org. Chem. 1991, 56, 5059.
22. (c) Harmata, M.; Kahraman, M. J. Org. Chem. 1998, 63, 6845.
23. (d) Harmata, M.; Kahraman, M.; Jones, D. E.; Pavri, N.; Weatherwax, S. E. Tetrahedron 1998, 54, 9995.
24. Klunder, J. M.; Sharpless, K. B. J. Org. Chem. 1987, 52, 2598.
25. Wantanabe, Y.; Mase, N.; Tateyama, M.; Toru, T. Tetrahedron Asymmetry 1999, 10, 737.
26. An enantioselective version of the reaction is conceivable, see: Nakamura, S.; Tateyama, M.; Sugimoto, H.; Nakagawa, M.; Watanabe, Y.; Shibata, N.; Toru, T. Chirality 2005, 17, 85 and references therein.
27. Though one might not expect such a reaction at low temperatures, see: Masaki, M.; Fukui, K.; Kita, J. Bull. Soc. Chem. Jpn. 1977, 50, 2013.
28. Garcia-Ruano, J.; Alonso, R.; Zarzuelo, M. M.; Noheda, P. Tetrahedron: Asymmetry 1995, 6, 1133.
29. Xiao, X.; Wang, H.; Huang, Z.; Yang, J.; Bian, X.; Qin, Y. Org. Lett. 2006, 8, 139.