The task-specific room-temperature ionic liquid (TSIL) N, N, N-trimethyl-N-butanesulfonic acid ammonium hydrogen sulfate [TMBSA]HSO4 was synthesized as a cheap and recyclable catalyst for one-pot three-component Mannich reaction in water. Sixteen β-amino carbonyl compounds were obtained in good yields under the mild conditions. The products could simply be separated from the catalyst/water, and the catalyst could be reused at least 7 times without noticeably decreasing the catalytic activity.
Similar content being viewed by others
References
For reviews of Mannich-type reaction, see: (a) S.E. Denmark, Nicaise, O.J.-C, in: Comprehensive Asymmetric Catalysis, eds. E.N. Jacobsen, A. Pfaltz and H. Yamamoto, (Springer: Heidelberg, 1999) pp. 923–961; (b) E.F. Kleinmann, in: Comprehensive Organic Synthesis, Vol. 2, ed. B.M. Trost, (Pergamon Press, New York 1991), Ch. 4.1; (c) M. Arend, B. Westermann, N. Risch, Angew. Chem. Int. Ed. 37, (1998) 1044; (d) S. Kobayashi, H. Ishitani, Chem. Rev. 99 (1999) 1069; (e) S. Kobayashi, M. Ueno, in: Comprehensive Asymmetric Catalysis, Supplement Vol. 1, (Springer: Berlin, 2004), pp.143–150; (f) A. Cordova, Acc. Chem. Res. 37 (2004) 102.
(a) N.E. Leadbeater, H.M. Torenius, H. Tye, Mol. Diversity 7 (2003) 135; (b) V. Aberg, H. Almstedt, A. Westermark, F. Almqvist, J. Org. Chem. 69 (2004) 7830.
D.-Y. Hu, B.-A. Song, G.-P. Zhang, S. Yang, W. He, Y.-L. Wu, Y.-P. Hong, L.-H. Jin, G. Liu (2005) Chin. J. Org. Chem. 25:845
(a) M. Shimizu and S. Itohara, Synlett (2000) 1828; (b) S. Kobayashi, T. Busujima and S. Nagayama, Synlett, 5 (1999) 545; (c) T.P. Loh and L.L. Wei, Tetrahedron Lett. 39 (1998) 323; (d). T.- P. Loh and S.- L. Chen, Org. Lett. 4 (2002) 3647; (e) I. Komoto and S. Kobayashi, Chem. Commun. 1842 (2001); (f) T. Ollevier and E. Nadeau, J. Org. Chem. 69 (2004) 9292; (g) M. Shi, S.-C. Cui and Q.-J. Li, Tetrahedron 60 (2004) 6163; (h) W.-B. Yi and C. Cai, J. Flu. Chem. 127 (2006) 1515; (i) L.M. Wang, J.W. Han, J. Sheng, Z.Y. Fan and H. Tian, Chin. J. Org. Chem. 25 (2005) 591; (j) T.J. Meng, L. Xin and J.X. Wang, J. SHANGQIU Teac. Coll. 22 (2006) 101.
Takahashi E., Fujisawa H., Mukaiyama T. (2004) Chem. Lett. 33:936
(a) R.O. Duthaler, Angew. Chem., Int. Ed. 42 (2003) 975; (b) L. Yi, H.S. Lei and J.H. Zou, Synthesis (1991) 717; (c) T. Akiyama, J. Takaya and H. Kagoshima, Adv. Synth. Catal. 344, (2002) 338; (d) S. Iimura, D. Nobutou, K. Manable and S. Kobayashi, Chem. Commun. 1644 (2003); (e) N. Azizi, L. Torkiyan, M.R. Saidi, Org. Lett. 8 (2006) 2079.
(a) B. Rodriguez, C. Bolm, J. Org. Chem. 71 (2006) 2888; (b) B. List, J. Am. Chem. Soc., 122 (2000) 9336; (c) B. List, P. Pojarliev, W.T. Biller, H.J. Martin, J. Am. Chem. Soc. 124 (2002) 827; (d) W. Notz, S.-I. Watanabe, N.S. Chowdari, G. Zhong, J.M. Betancort, F. Tanaka, C.F. Barbas III, Adv. Synth. Catal. 346 (2004) 1131; (e) S. Mitsumori, H. Zhang, P.H.-Y. Cheong, K.N. Houk, F. Tanaka, C.F. Barbas III, J. Am. Chem. Soc. 128 (2006) 1040; (f) I. Ibrahem, J. Casas, A. Córdova, Angew. Chem. Int. Ed. 43 (2004) 6528.
(a) T. Welton, Chem. Rev. 99 (1999) 2071; (b) P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 39 (2000) 3773; (c) E.D. Bates, R.D. Mayton, I. Ntai, J.H. Davis, J. Am. Chem. Soc. 124 (2002) 926; (d) A.C. Cole, J.L. Jensen, I. Ntai, T. Tran, K.J. Weaver, D.C. Forbes, J.H. Davis Jr., J. Am. Chem. Soc. 124 (2002) 5962.
T. Akiyama, A. Suzuki, K. Fuchibe, Synlett, (2005) 1024.
Yang X.-F., Wang M., Varma R.S., Li C.-J. (2004) J. Mol. Catal. A: Chem. 214:147
Lee S.-Gi., Park J.H. (2002) Bull. Kor. Chem. Soc. 23:1367
Zhao G., Jiang T., Gao H., Han B., Huang J., Sun D. (2004) Green Chem. 6:75
Li J., Peng Y., Song G. (2005) Catal. Lett. 102:159
Sahoo S., Joseph T., Halligudi S.B. (2006) J. Mol. Catal. A: Chem. 244:179
(a) M.T. Garcia, N. Gathergood, P. J. Scammells, Green Chem. 5 (2005) 9; (b) N. Gathergood, M.T. Garcia, P.J. Scammells, Green Chem. 6 (2004) 166; (c) P. Wasserscheid, R. Hal, A. Bösmann, Green Chem. 4 (2002) 400; (d) J. Fraga-Dubreuil, K. Bourahla, M. Rahmouni, J.P. Bazureau, J. Hamelin, J. Catal. Commun. 3 (2002) 185
(a). D. Fang, K. Gong, Q. R. Shi, Z. L. Liu, Catal. Commun.(2007) doi: 10.1016/ j.catcom. 2006.12.019; (b). D. Fang, Z. L. Liu, X. L. Zhou, Chin. J. Appl. Chem. 24 (2007) 85
Acknowledgments
The financial supports from the Nanjing University of Science & Technology (N0. 2006001) and Yancheng Teachers College are gratefully acknowledged.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Dong, F., Jun, L., Xin-Li, Z. et al. Mannich reaction in water using acidic ionic liquid as recoverable and reusable catalyst. Catal Lett 116, 76–80 (2007). https://doi.org/10.1007/s10562-007-9095-8
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-007-9095-8