A facile and green protocol for nucleophilic substitution reactions of sulfonate esters by recyclable ionic liquids [bmim][X]

Synlett

Volumn 23, Issue 18, 2012, Pages 2692-2698

  Liu, Yajun ^a,b   Xu, Yongnan ^a   Jung, Sun Ho ^b   Chae, Junghyun ^b  

^a SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

^b Sungshin Women's University   (South Korea)

Author keywords

green chemistry; halogenation; ionic liquids; nucleophilic substitution; recyclability

Indexed keywords

1 PHENYLPROPAN 2 YL METHANESULFONATE; 3 PHENYLPROPYL METHANESULFONATE; ACETIC ACID; BROMINE; HALIDE; IONIC LIQUID; SULFONATE ESTER; SULFONIC ACID DERIVATIVE; THIOCYANATE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; GREEN CHEMISTRY; HALOGENATION; NUCLEOPHILICITY; REACTION TIME; RECYCLING; STEREOCHEMISTRY; STOICHIOMETRY; SUBSTITUTION REACTION;

EID: 84867681962     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1317473     Document Type: Article

References (47)

1. Wasserscheid P., Keim W. Angew. Chem. Int. Ed.: 2000; 39 3772
2. Plechkova N. V., Seddon K. R. Chem. Soc. Rev.: 2008; 37 123
3. Carlos K. Z. A, Luana M. A. Curr. Org. Chem.: 2005; 9 195
4. Olivier-Bourbigou H., Magna L. J. Mol. Catal. A: Chem.: 2002; 182-183 419
5. Rebelo L. P. N, Canongia Lopes J. N., Esperança J. M. S. S, Filipe E. J. Phys. Chem. B: 2005; 109 6040
6. Fredlake C. P., Crosthwaite J. M., Hert D. G., Aki S. N. V. K, Brennecke J. F. J. Chem. Eng. Data: 2004; 49 954
7. Wu B., Liu W., Zhang Y., Wang H. Chem.-Eur. J.: 2009; 15 1804
8. Earle M. J., McCormac P. B., Seddon K. R. Green Chem.: 1999; 1 23
9. Zhu H.-P, Yang F., Tang J., He M.-Y. Green Chem.: 2003; 5 38
10. Rosa J. N., Afonso C. A. M, Santos A. G. Tetrahedron: 2001; 57 4189
11. Davis J. J. H. Chem. Lett.: 2004; 33 1072
12. Luo S., Mi X., Zhang L., Liu S., Xu H., Cheng J.-P. Angew. Chem. Int. Ed.: 2006; 45 3093
13. Luo S., Zhang L., Cheng J.-P. Chem.-Asian J.: 2009; 4 1184
14. Fei Z., Geldbach T. J., Zhao D., Dyson P. J. Chem.-Eur. J.: 2006; 12 2122
15. Li X., Zhao D., Fei Z., Wang L. Sci. China Ser. B: Chem.: 2006; 49 385
16. Song C. E. Chem. Commun.: 2004; 1033
17. Kotti S. R. S. S, Xu X., Wang Y., Headley A. D., Li G. Tetrahedron Lett.: 2004; 45 7209
18. Ranu B. C., Banerjee S. J. Org. Chem.: 2005; 70 4517
19. Revell J. D., Ganesan A. Org. Lett.: 2002; 4 3071
20. Welton T. Chem. Rev.: 1999; 99 2071
21. Hallett J. P., Welton T. Chem. Rev.: 2011; 111 3508
22. Earle M. J., Seddon K. R. Pure Appl. Chem.: 2000; 72 1391
23. Jorapur Y. R., Chi D.-Y. Bull. Korean Chem. Soc.: 2006; 27 345
24. Pârvulescu V. I., Hardacre C. Chem. Rev.: 2007; 107 2615
25. Dupont J., de Souza R. F., Suarez P. A. Z. Chem. Rev.: 2002; 102 3667
26. Miao W., Chan T. H. Acc. Chem. Res.: 2006; 39 897
27. Sheldon R. Chem. Commun.: 2001; 2399
28. Sheldon R. A., Lau R. M., Sorgedrager M. J., van Rantwijk F., Seddon K. R. Green Chem.: 2002; 4 147
29. Gribble G. W. J. Chem. Educ.: 2004; 81 1441
30. Hernandes M. Z., Cavalcanti S. M. T, Moreira D. R. M, Junior W. F. A, Leite A. C. L. Curr. Drug Targets: 2010; 11 303
31. Häggblom M. M., Bossert I. D. Dehalogenation: Microbial Processes and Environmental Applications. Springer New York: 2004; 3
32. Spargo P. L. In Comprehensive Organic Functional Group Transformations. Vol. 2 Katritzky A. R., Meth-Cohn O., Rees C. W. Pergamon Oxford: 1995; 9
33. Larock R. C. Comprehensive Organic Functional Group Transformations. Wiley New York: 1999; 697
34. Ortega N., Feher-Voelger A., Brovetto M., Padrón J. I., Martín V. S., Martín T. Adv. Synth. Catal.: 2011; 353 963
35. San Filippo J., Romano L. J. J. Org. Chem.: 1975; 40 1514
36. Landini D., Quici S., Rolla F. Synthesis: 1975; 430
37. Jadhav V. H., Jang S. H., Jeong H. J., Lim S. T., Sohn M. H., Chi D. Y., Kim D. W. Org. Lett.: 2010; 12 3740
38. Jadhav V. H., Jeong H. J., Lim S. T., Sohn M. H., Kim D. W. Org. Lett.: 2011; 13 2502
39. Kim D. W., Chi D. Y. Angew. Chem. Int. Ed.: 2004; 43 483
40. Kim D. W., Song C. E., Chi D. Y. J. Am. Chem. Soc.: 2002; 124 10278
41. Kim D. W., Song C. E., Chi D. Y. J. Org. Chem.: 2003; 68 4281
42. Shinde S. S., Lee B. S., Chi D. Y. Org. Lett.: 2008; 10 733
43. Gupta N., Kad G. L., Singh J. J. Mol. Catal. A: Chem.: 2009; 302 11
44. Nguyen H.-P, Matondo N. H., Baboulene M. Green Chem.: 2003; 5 303
45. Lancaster N. L., Salter P. A., Welton T., Young G. B. J. Org. Chem.: 2002; 67 8855
46. Lancaster N. L., Welton T. J. Org. Chem.: 2004; 69 5986
47. Lancaster N. L., Welton T., Young G. B. J. Chem. Soc., Perkin Trans. 2: 2001; 2267