Synthesis of 1,3-Dialkyl-1,2,3-triazolium ionic liquids and their applications to the baylis-hillman reaction

Journal of Organic Chemistry

Volumn 75, Issue 12, 2010, Pages 4183-4191

  Jeong, Yunkyung ^a   Ryu, Jae Sang ^a  

^a Ewha Womans University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

[BMIM][PF; BASIC CONDITIONS; BAYLIS-HILLMAN REACTIONS; CLICK REACTION; DIALKYLIMIDAZOLIUM; REACTION MEDIA;

HYDROCARBONS; IONIZATION OF LIQUIDS; IONS; SYNTHESIS (CHEMICAL);

IONIC LIQUIDS;

1 BENZYL 3 METHYL 1,2,3 TRIAZOLIUM BIS(TRIFLUOROMETHYLSULFONYL)AMIDE; 1 BENZYL 3 METHYL 1,2,3 TRIAZOLIUM HEXAFLUOROPHOSPHATE; 1 BENZYL 3 METHYL 1,2,3 TRIAZOLIUM IODIDE; 1 BENZYL 3 METHYL 1,2,3 TRIAZOLIUM TETRAFLUOROBORATE; 1 BENZYL 3 METHYL 1,2,3 TRIAZOLIUM TRIFLUOROMETHYLSULFONATE; 1 BUTYL 3 METHYL 1,2,3 TRIAZOLIUM BIS(TRIFLUOROMETHYLSULFONYL)AMIDE; 1 BUTYL 3 METHYL 1,2,3 TRIAZOLIUM HEXAFLUOROPHOSPHATE; 1 BUTYL 3 METHYL 1,2,3 TRIAZOLIUM IODIDE; 1 BUTYL 3 METHYL 1,2,3 TRIAZOLIUM TETRAFLUOROBORATE; 1 BUTYL 3 METHYL 1,2,3 TRIAZOLIUM TRIFLUOROMETHYLSULFONATE; 1,3 DIBUTYL 1,2,3 TRIAZOLIUM BIS(TRIFLUOROMETHYLSULFONYL)AMIDE; 1,3 DIBUTYL 1,2,3 TRIAZOLIUM HEXAFLUOROPHOSPHATE; 1,3 DIBUTYL 1,2,3 TRIAZOLIUM IODIDE; 1,3 DIBUTYL 1,2,3 TRIAZOLIUM TETRAFLUOROBORATE; 1,3 DIBUTYL 1,2,3 TRIAZOLIUM TRIFLUOROMETHYLSULFONATE; BASE; HYDROGEN; IONIC LIQUID; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; SYNTHESIS;

ALKANES; IONIC LIQUIDS; MOLECULAR STRUCTURE; TRIAZOLES;

EID: 77953507131     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100618d     Document Type: Article

References (26)

1. For reviews, see: Basavaiah, D.; Rao, K. V.; Reddy, R. J. Chem. Soc. Rev. 2007, 36, 1581-1588
2. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891
3. Baylis, A. B.; Hillman, M. E. D. Ger. Offen. 2 155 113, 1972.
4. Hillman, M. E. D.; Baylis, A. B. US Patent 3 743 669, 1973.
5. Morita, K.; Suzuki, Z.; Hirose, H. Bull. Chem. Soc. Jpn. 1968, 41, 2815
6. Rauhut, M.; Currier, H. US Patent 3 074 999, 1963.
7. Yu, C.; Liu, B.; Hu, L. J. Org. Chem. 2001, 66, 5413-5418
8. Krishna, P. R.; Manjuvani, A.; Kannan, V.; Sharma, G. V. M. Tetrahedron Lett. 2004, 45, 1183-1185
9. Rose, P. M.; Clifford, A. A.; Rayner, C. M. Chem. Commun. 2002, 968-969
10. Chandrasekhar, S.; Narsihmulu, C.; Saritha, B.; Sultana, S. S. Tetrahedron Lett. 2004, 45, 5865-5867
11. Ge, S.-Q.; Hua, Y.-Y.; Xia, M. Ultrason. Sonochem. 2009, 16, 743-746
12. Kundu, M. K.; Mukherjee, S. B.; Balu, N.; Padmakumar, R.; Bhat, S. V. Synlett 1994, 444
13. Chowdhury, S.; Mohan, R. S.; Scott, J. L. Tetrahedron 2007, 63, 2363-2389 and references therein.
14. Sugden, S.; Wilkins, H. J. Chem. Soc. 1929, 1291-1298 and references therein.
15. Santos, L. S.; Da Silveira Neto, B. A.; Consorti, C. S.; Pavam, C. H.; Almeida, W. P.; Coelho, F.; Dupont, J.; Eberlin, M. N. J. Phys. Org. Chem. 2006, 19, 731-736
16. Aggarwal, V. K.; Emme, I.; Mereu, A. Chem. Commun. 2002, 1612-1613
17. Hsu, J.-C.; Yen, Y.-H.; Chu, Y.-H. Tetrahedron Lett. 2004, 45, 4673-4676
18. Handy, S. T.; Okello, M. J. Org. Chem. 2005, 70, 1915-1918
19. Jurčík, V.; Wilhelm, R. Green Chem. 2005, 7, 844-848
20. For 1,3,4-trialkyl-1,2,3-triazolium and pyrrolidine-tethered 1,3,4-trialkyl-1,2,3-triazolium, see: Hanelt, S.; Liebscher, J. Synlett 2008, 1058-1060
21. Yacob, Z.; Shah, J.; Leistner, J.; Liebscher, J. Synlett 2008, 2342-2344
22. 6] is commercially available, and the melting point obtained from the Aldrich database is 136 °C.
23. 4] is commercially available, and the melting point obtained from Aldrich database is 77 °C.
24. Rosa, J. N.; Afonso, C. A. M.; Santos, A. G. Tetrahedron 2001, 57, 4189-4193
25. The rapid decomposition of the product 19d was also reported in the literature; see: Aggarwal, V. K.; Emme, I.; Fulford, S. Y. J. Org. Chem. 2003, 68, 692-700
26. Earle, M. J.; Gordon, C. M.; Plechkova, N. J.; Seddon, K. R.; Welton, T. Anal. Chem. 2007, 79, 758-764