Introducing difluoromethylene sulfonamide group via nucleophilic addition of difluoromethylene anion with aromatic aldehydes

Tetrahedron

Volumn 63, Issue 4, 2007, Pages 898-903

  Li, Jun Li ^a   Liu, Jin Tao ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Aldehyde; Difluoromethylene; Difluoromethylene containing alcohol; Potassium tert butoxide

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; DIFLUOROMETHYLENE SULFONAMIDE; FLUORINE; ORGANIC COMPOUND; POTASSIUM DERIVATIVE; SULFONAMIDE;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; PRIORITY JOURNAL; QUANTUM YIELD;

EID: 33845388351     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.11.036     Document Type: Article

References (34)

1. Welch J.T., and Eswarakrishman S. Fluorine in Bioorganic Chemistry (1991), Wiley, New York, NY
2. Filler R., Kobayashi Y., and Yagupolskii L.M. Organofluorine Compounds in Medicinal Chemistry and Biochemical Applications (1993), Elsevier, Amsterdam
3. Banks R.E., Smart B.E., and Tatlow J.C. Organofluorine Chemistry: Principles and Commercial Applications (1994), Plenum, New York, NY
4. Welch J.T. Selective Fluorination in Organic and Bioorganic Chemistry (1990), American Chemical Society, Washington, DC
5. Ojima I., McCarthy J.R., and Welch J.T. Biomedical Frontiers of Fluorine Chemistry (1996), American Chemical Society, Washington, DC
6. Tozer M.J., and Herpin T.F. Tetrahedron 52 (1996) 8619-8683
7. Burton D.J., Yang Z.Y., and Qiu W. Chem. Rev. 96 (1996) 1641-1715
8. Plantier-Royon R., and Portella C. Carbohydr. Res. 327 (2000) 119-146
9. Berkowitz D.B., Bhuniya D., and Peris G. Tetrahedron Lett. 40 (1999) 1869-1872
10. Mikami K., Itoh Y., and Yamanaka M. Chem. Rev. 104 (2004) 1-16
11. Wang Z.G., and Hammond G.B. Chem. Commun. (1999) 2545-2546
12. Itoh T., Kudo K., Tanaka N., Sakabe K., Takagi Y., and Kihara H. Tetrahedron Lett. 41 (2000) 4591-4595
13. Staas D.D., Savage K.L., Homnick C.F., Tsou N.N., and Ball R.G. J. Org. Chem. 67 (2002) 8276-8279
14. Cox L.R., DeBoos G.A., Fullbrook J.J., and Percy J.M. Org. Lett. 5 (2003) 337-339
15. Prakash G.K.S., Hu J., Mathew T., and Olah G.A. Angew. Chem., Int. Ed. 42 (2003) 5216-5219
16. Yudin A.K., Prakash G.K.S., Deffieux D., Bradley M., Bau R., and Olah G.A. J. Am. Chem. Soc. 119 (1997) 1572-1581
17. Moree W.J., van der Marel G.A., and Liskamp R.M.J. Tetrahedron Lett. 32 (1991) 409-412
18. Zecchini G.P., Paradisi M.P., Torrini I., Lucente G., Gavuzzo E., Mazza F., and Pochetti G. Tetrahedron Lett. 32 (1991) 6779-6782
19. Moree W.J., van der Marel G.A., and Liskamp R.J. J. Org. Chem. 60 (1995) 5157-5169
20. Gennari C., Nestler H.P., Salom B., and Still W.C. Angew. Chem., Int. Ed. Engl. 34 (1995) 1765-1768
21. Langlois B.R., and Billard T. Synthesis (2003) 185-193
22. Jablonski L., Joubert J., Billard T., and Langlois B.R. Synlett (2003) 230-232
23. Inschauspe D., Sortais J.-P., Billard T., and Langlois B.R. Synlett (2003) 233-235
24. Jablonski L., Billard T., and Langlois B.R. Tetrahedron Lett. 44 (2003) 1055-1057
25. Joubert J., Roussel S., Christophe C., Billard T., Langlois B.R., and Vidal T. Angew. Chem., Int. Ed. 42 (2003) 3133-3136
26. Prakash G.K.S., Hu J., and Olah G.A. Org. Lett. 5 (2003) 3253-3256
27. Chen Q., and Wu S. J. Chem. Soc., Chem. Commun. (1989) 705-706
28. Chen Q., and Duan J. J. Chem. Soc., Chem. Commun. (1993) 918-919
29. Duan J., Dolbier W.R., and Chen Q. J. Org. Chem. 63 (1998) 9486-9489
30. Xu W., and Chen Q. J. Org. Chem. 67 (2002) 9421-9427
31. Tian F., Kruger V., Bautista O., Duan J., Li A., Dolbier W.R., and Chen Q. Org. Lett. 2 (2000) 563-564
32. Roche A.J., and Dolbier W.R. J. Org. Chem. 65 (2000) 5282-5290
33. Veliz E.A., Stephens O.M., and Beal P.A. Org. Lett. 3 (2001) 2969-2972
34. Wu T.R., Shen L., and Chong J.M. Org. Lett. 6 (2004) 2701-2704