Brønsted acid ionic liquid as a solvent-conserving catalyst for organic reactions

ChemSusChem

Volumn 7, Issue 8, 2014, Pages 2094-2098

  Taheri, Amir ^a   Pan, Xiaojuan ^a   Liu, Changhui ^a   Gu, Yanlong ^a,b  

^a HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

acid catalysis; biphasic catalysis; green chemistry; ionic liquid

Indexed keywords

CATALYSIS; IONIC LIQUIDS;

ACID CATALYSIS; BIPHASIC CATALYSIS; CATALYST SYSTEM; GREEN CHEMISTRY; HETEROGENEOUS CATALYST; ORGANIC REACTION; REACTION SYSTEM;

CATALYSTS;

AMMONIUM DERIVATIVE; IONIC LIQUID; ORGANIC COMPOUND;

CATALYSIS; CHEMISTRY; PH;

AMMONIUM COMPOUNDS; CATALYSIS; HYDROGEN-ION CONCENTRATION; IONIC LIQUIDS; ORGANIC CHEMICALS;

EID: 84905995498     PISSN: 18645631     EISSN: 1864564X     Source Type: Journal    
DOI: 10.1002/cssc.201402220     Document Type: Article

References (46)

1. J. F. Brennecke, E. J. Maginn, AIChE J. 2001, 47, 2384-2389.
2. F. M. Kerton, Alternative Solvents for Green Chemistry, RSC Green Chemistry Series, Series Editors: J. Clark, 2009
3. Green Solvents for Chemistry-Perspectives and Practice (Ed.:, M. N. William,), 2003, Oxford University Press, USA.
4. See some reviews: a) M. A. P. Martins, C. P. Frizzo, D. N. Moreira, L. Buriol, P. Machado, Chem. Rev. 2009, 109, 4140-4192
5. K. Tanaka, F. Toda, Chem. Rev. 2000, 100, 1025-1074
6. A. Loupy, Top. Curr. Chem. 1999, 206, 153-207.
7. A. C. Cole, L. L. Jensen, I. Ntai, K. L. T. Tran, K. J. Weaver, D. C. Forbes, J. H. Davis, Jr., J. Am. Chem. Soc. 2002, 124, 5962-5963
8. D. Chaturvedi, Curr. Org. Chem. 2011, 15, 1236-1248
9. A. R. Hajipour, F. Rafiee, Org. Prep. Proced. Int. 2010, 42, 285-362.
10. See some recent examples: a) S. Safaei, I. Mohammadpoor-Baltork, A. R. Khosropour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, Adv. Synth. Catal. 2012, 354, 3095-3104
11. S. Zhang, A. Feret, H. Lefebvre, M. Tessier, A. Fradet, Chem. Commun. 2011, 47, 11092-11094
12. R. G. Kalkhambkar, S. N. Waters, K. K. Laali, Tetrahedron Lett. 2011, 52, 867-871
13. X. Nie, X. Liu, L. Gao, M. Liu, C. Song, X. Guo, Ind. Eng. Chem. Res. 2010, 49, 8157-8163.
14. Many carbocation intermediates are more stable in polar aprotic solvents, see: a) N. Streidl, H. Mayr, Eur. J. Org. Chem. 2011, 2498-2506
15. N. Streidl, B. Denegri, O. Kronja, H. Mayr, Acc. Chem. Res. 2010, 43, 1537-1549
16. K. S. Peters, Chem. Rev. 2007, 107, 859-873
17. J. P. Richard, M. M. Toteva, T. L. Amyes, Org. Lett. 2001, 3, 2225-2228.
18. See a recent example in which Brønsted acid IL catalyst has to be used in organic solvent otherwise its performance will be diminished significantly:, S. E. Sim, S. Kwon, S. Koo, Molecules 2012, 17, 12804-12811. Many acid-catalyzed reactions have to be performed in polar aprotic solvents, see a recent review
19. R. R. Naredla, D. A. Klumpp, Chem. Rev. 2013, 113, 6905-6948; See some selected examples
20. B. V. Rokade, K. R. Prabhu, J. Org. Chem. 2012, 77, 5364-5370
21. R. Niu, J. Xiao, T. Liang, X. Li, Org. Lett. 2012, 14, 676-679
22. H. L. Yue, W. Wei, M. M. Li, Y. R. Yang, J. X. Ji, Adv. Synth. Catal. 2011, 353, 3139-3145
23. M. N. Lin, S. H. Wu, M. C. P. Yeh, Adv. Synth. Catal. 2011, 353, 3290-3294
24. A. Yanagisawa, T. Nezu, S. I. Mohri, Org. Lett. 2009, 11, 5286-5289
25. O. Scadeng, M. J. Ferguson, F. G. West, Org. Lett. 2011, 13, 114-117
26. M. Yoshida, Y. Fujino, T. Doi, Org. Lett. 2011, 13, 4526-4529
27. L. Wang, X. Xie, Y. Liu, Org. Lett. 2012, 14, 5848-5851
28. T. Aoyama, S. Koda, Y. Takeyoshi, T. Ito, T. Takido, M. Kodomari, Chem. Commun. 2013, 49, 6605-6607.
29. See the Supporting Information: a) S. K. Xiang, L. H. Zhang, N. Jiao, Chem. Commun. 2009, 6487-6489.
30. K. Ren, P. Li, L. Wang, X. Zhang, Tetrahedron 2011, 67, 2753-2759.
31. Y. Gu, J. Zhang, Z. Duan, Y. Deng, Adv. Synth. Catal. 2005, 347, 512-516
32. C. Thomazeau, H. Olivier-Bourbigou, L. Magna, S. Luts, B. Gilbert, J. Am. Chem. Soc. 2003, 125, 5264-5265.
33. G. Chatel, R. Pflieger, E. Naffrechoux, S. I. Nikitenko, J. Suptil, C. Goux-Henry, N. Kardos, B. Andrioletti, M. Draye, ACS Sustainable Chem. Eng. 2013, 1, 137-143
34. A. O. Diallo, A. B. Morgan, A. Len, G. Marlair, Energy Environ. Sci. 2013, 6, 699-710.
35. Such responses to aromatics by the imidazolium-based ILs have been reported and ascribed to the formation of liquid clathrates:, J. D. Holbrey, W. M. Reichert, M. Nieuwenhuyzen, O. Sheppard, C. Hardacre, R. D. Rogers, Chem. Commun. 2003, 476-477.
36. Both Brønsted acid and Lewis acid catalysts have been used in this reaction, please see: a) S. L. Zhang, Z. F. Xue, Y. R. Gao, S. Mao, Y. Q. Wang, Tetrahedron Lett. 2012, 53, 2436-3439
37. Y. Zhao, J. Li, C. Li, K. Yin, D. Ye, X. Jia, Green Chem. 2010, 12, 1370-1372
38. A. Kumar, M. Dixit, S. P. Singh, R. Raghunandan, P. R. Maulik, A. Goel, Tetrahedron Lett. 2009, 50, 4335-4339
39. N. Iranpoor, B. Zeynizaded, Synlett 1998, 1079-1080
40. Z. Li, W. H. Sun, X. Jin, C. Shao, Synlett 2001, 1947-1949
41. F. Ono, Y. Ishikura, Y. Tada, M. Endo, T. Sato, Synlett 2008, 2365-2367
42. R. Qiu, X. Xu, L. Peng, Y. Zhao, N. Li, S. Yin, Chem. Eur. J. 2012, 18, 6172-6182.
43. L. Cui, Y. Zhu, S. Luo, J. Cheng, Chem. Eur. J. 2013, 19, 9481-9484
44. H. E. Zimmerman, T. Novak, J. Org. Chem. 2003, 68, 5056-5066
45. E. Ishai, S. Shamai, B. A. Feit, J. Chem. Soc. Perkin Trans. 1 2002, 434-438.
46. B. Qian, G. Zhang, Y. Ding, H. Huang, Chem. Commun. 2013, 49, 9839-9841.