Chlorination of aromatics with trichloroisocyanuric acid (TCICA) in brønsted-acidic imidazolium ionic liquid [BMIM(SO3H)][OTf]: An economical, green protocol for the synthesis of chloroarenes

Australian Journal of Chemistry

Volumn 60, Issue 12, 2007, Pages 923-927

  Hubbard, Abigail ^a   Okazaki, Takao ^a   Laali, Kenneth K ^a  

^a KENT STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINATION; IONIC LIQUIDS; ORGANIC ACIDS; REACTION KINETICS; SUBSTRATES; SYNTHESIS (CHEMICAL);

CHEMOSELECTIVITY; CHLOROARENES; TRICHLOROISOCYANURIC ACID;

AROMATIC COMPOUNDS;

EID: 36749021743     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH07261     Document Type: Article

References (29)

1. J. C. Barros Synlett 2005, 2115. doi:10.1055/S-2005-872237
2. G. K. S. Prakash, T. Mathew, D. Hoole, P. M. Esteves, Q. Wang, G. Rasul, G. A. Olah, J Am. Chem. Soc. 2004, 126, 15770. doi:10.1021/JA0465247
3. G. A. Hiegel, J. Ramirez, R. K. Barr, Synth. Commun. 1999, 29, 1415. doi:10.1080/00397919908086119
4. O. Sugimoto, K. Tanji, Heterocycles 2005, 65, 181.
5. (a) T. Umemoto, in Advances in Organic Synthesis (Ed. K. K. Laali) 2006, Vol. 2, pp. 159-181 (Bentham: the Netherlands).
6. (b) S. Stavber, M. Zupan, in Advances in Organic Synthesis (Ed. K. K. Laali) 2006, Vol. 2, pp. 213-268 (Bentham: the Netherlands).
7. G. F. Mendonça, R. R. Magalhães, M. C. S. de Mattos, P. M. Esteves, J Braz. Chem. Soc. 2005, 16, 695.
8. (a) A. C. Cole, J. 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. doi:10.1021/JA026290W
9. (b) Z. Du, Z. Li, Y. Deng, Synth. Commun. 2005, 35, 1343. doi:10.1081/SCC-200057264
10. (c) S. Chowdhury, R. S. Ram, J. L. Scott, Tetrahedron 2007, 63, 2363. doi:10.1016/J.TET.2006.11.001
11. (a) K. Qiao, C. Yokoyama, Chem. Lett. (Jpn.) 2004, 33, 1350. doi:10.1246/CL.2004.808
12. (b) K. Qiao, C. Yokoyama, Chem. Lett. (Jpn.) 2004, 33, 472. doi:10.1246/CL.2004.472
13. (c) K. Qiao, Y. Deng, C. Yokoyama, H. Sato, M. Yamashima, Chem. Lett. (Jpn.) 2004, 33, 472, doi:10.1246/CL.2004.472
14. H.-P. Zhu, F. Yang, M. Y. He, Green Chem. 2003, 5, 38. doi:10.1039/B209248B
15. (a) Y Gu, F. Shi, Y. Deng, Catai. Commun. 2003, 4, 597. doi:10.1016/XCATCOM.2003.09.004
16. (b) Y. Gu, F. Shi, Y. Deng, J. Mol. Catal. A-Chem. 2004, 272, 71. doi:10.1016/J.MOLCATA.2003.10.039
17. T.M. Potewar, R. J. Lahoti, T.Daniel, K.V. Srinivasen, Synth. Commun. 2007, 37, 261. doi:10.1080/00397910601033534
18. K. K. Laali, V. J. Gettwert, J. Fluorine Chem. 2001, 107, 31. doi:10.1016/S0022-1139(00)00337-7
19. K. K. Laali, V. J. Gettwert, J. Org. Chem. 2001, 66, 35. doi:10.1021/JO000523P
20. K. K. Laali, G. I. Borodkin, J. Chem. Soc., Perkin Trans. 2 2002, 953. doi:10.1039/B111725D
21. V. D. Sarca, K. K. Laali, Green Chem. 2004, 6, 245. doi:10.1039/B400113C
22. K. K. Laali, V. D. Sarca, T. Okazaki, A. Brock, P. Der, Org. Biomol. Chem. 2005, 3, 1034. doi:10.1039/B416997B
23. V. D. Sarca, K. K. Laali, Green Chem. 2006, 8, 615. doi:10.1039/B603176E
24. K. K. Laali, in Ionic Liquids in Organic Synthesis: ACS Symposium Ser. 950 (Ed. S. V. Malhotra) 2006, Ch. 2 (ACS: Washington, DC).
25. K. K. Laali, T. Okazaki, S. D. Bunge, J Org. Chem. 2007, 72, 6758. doi:10.1021/JO0708801
26. P. Kralj, M. Zupan, S. Stavber, J Org. Chem. 2006, 71, 3880. doi:10.1021/JO060213S
27. A. J. Bellamy, N. V. Latypov, P. Goede, J. Chem. Res., Miniprint 2003, 9, 943.
28. W. Koch, M. C. Holthausen, A Chemist's Guide to Density Functional Theory, 2nd edn 2000 (Wiley-VCH: Weinheim).
29. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr, T. Vreven, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision B.05 2003 (Gaussian Inc.: Pittsburgh, PA).