Asian Journal of Chemistry
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Vol. 27 No. 8 (2015): Vol 27 Issue 8

Issue Published : April 27, 2015

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Silica Sulfuric Acid-Catalyzed One-Pot Synthesis of 1,3-Diarylimidazolium Tetrafluoroborate

https://doi.org/10.14233/ajchem.2015.18954

Yu Wan

State Key Laboratory Cultivation Construction Base of Biotechnology on Med-edible Plant of Jiangsu Province, Jiangsu Normal University, Xuzhou 221116, P.R. China

Wen-Li Zhang

School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou 221116, P.R. China

Hao Cui

School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou 221116, P.R. China

Li-Zhuo Zhang

School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou 221116, P.R. China

Qiu-Ju Zhou

School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou 221116, P.R. China

Huan Zou

School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou 221116, P.R. China

Yuan-Jiang Wang

School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou 221116, P.R. China

Wen-Hui Ge

School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou 221116, P.R. China

Yue Fang

School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou 221116, P.R. China

Sheng-Liang Zhou

State Key Laboratory Cultivation Construction Base of Biotechnology on Med-edible Plant of Jiangsu Province, Jiangsu Normal University, Xuzhou 221116, P.R. China

Hui Wu

School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou 221116, P.R. China; State Key Laboratory Cultivation Construction Base of Biotechnology on Med-edible Plant of Jiangsu Province, Jiangsu Normal University, Xuzhou 221116, P.R. China

Corresponding Author(s) : Yu Wan

Asian Journal of Chemistry, Vol. 27 No. 8 (2015): Vol 27 Issue 8
Article Published : April 28, 2015

Abstract

A silica sulfuric acid-catalyzed three-component one-pot synthesis of 1,3-diarylimidazolium tetrafluoroborates was undertaken via the reaction of aromatic amine, formaldehyde and glyoxal at room temperature in ionic liquid [BMIM][BF₄] with good yields. Up to four new bonds and one new ring were formed in one-pot with water as the only by-product in the reactions. The product 4d was determined by X-ray diffraction. This work develops an efficient and low-cost preparation of 1,3-diarylimidazolium and N-heterocylic carbene.

Keywords

Synthesis Silica sulfuric acid 1 3-Diarylimidazolium tetrafluoroborate

Wan, Y., Zhang, W.-L., Cui, H., Zhang, L.-Z., Zhou, Q.-J., Zou, H., … Wu, H. (2015). Silica Sulfuric Acid-Catalyzed One-Pot Synthesis of 1,3-Diarylimidazolium Tetrafluoroborate. Asian Journal of Chemistry, 27(8), 3107–3110. https://doi.org/10.14233/ajchem.2015.18954

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References

A.J. Arduengo, R.L. Harlow and M. Kline, J. Am. Chem. Soc., 113, 361 (1991); doi:10.1021/ja00001a054.
(a) F.E. Hahn and M.C. Jahnke, Angew. Chem. Int. Ed., 47, 3122 (2008); doi:10.1002/anie.200703883; (b) W.A. Herrmann, Angew. Chem. Int. Ed., 41, 1290 (2002); doi:10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y.
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V. Nair, S. Bindu and V. Sreekumar, Angew. Chem. Int. Ed., 43, 5130 (2004); doi:10.1002/anie.200301714.
(a) D. Enders, O. Niemeier and A. Henseler, Chem. Rev., 107, 5606 (2007); doi:10.1021/cr068372z; (b) N. Marion, S. Díez-González and S.P. Nolan, Angew. Chem. Int. Ed., 46, 2988 (2007); doi:10.1002/anie.200603380.
(a) L. Jafarpour and S.P. Nolan, Adv. Organomet. Chem., 46, 181 (2000); doi:10.1016/S0065-3055(00)46004-1; (b) W.A. Herrmann, T. Weskamp and V.P.W. Böhm, Adv. Organomet. Chem., 48, 1 (2001); doi:10.1016/S0065-3055(01)48001-4; (c) C.M. Crudden and D.P. Allen, Coord. Chem. Rev., 248, 2247 (2004); doi:10.1016/j.ccr.2004.05.013; (d) N.M. Scott and S.P. Nolan, Eur. J. Inorg. Chem., 1815 (2005); doi:10.1002/ejic.200500030; (e) J.C. Garrison and W.J. Youngs, Chem. Rev., 105, 3978 (2005); doi:10.1021/cr050004s; (f) V. Dragutan, I. Dragutan, L. Delaude and A. Demonceau, Coord. Chem. Rev., 251, 765 (2007); doi:10.1016/j.ccr.2006.09.002.
(a) D. Enders and T. Balensiefer, Acc. Chem. Res., 37, 534 (2004); doi:10.1021/ar030050j; (b) V. César, S. Bellemin-Laponnaz and L.H. Gade, Chem. Soc. Rev., 33, 619 (2004); doi:10.1039/b406802p.
A. Aidouni, S. Bendahou, A. Demonceau and L. Delaude, J. Comb. Chem., 10, 886 (2008); doi:10.1021/cc800101k.
P.I. Dalko and L. Moisan, Angew. Chem. Int. Ed., 43, 5138 (2004); doi:10.1002/anie.200400650.
V. Jurčík and R. Wilhelm, Org. Biomol. Chem., 3, 239 (2005); doi:10.1039/b415023f.
S. Jacobsen, P.H. Degee, H.G. Fritz, P.H. Dubois and R. Jerome, Polym. Eng. Sci., 39, 1311 (1999); doi:10.1002/pen.11518.
M.S. Kerr, J. Read de Alaniz and T. Rovis, J. Am. Chem. Soc., 124, 10298 (2002); doi:10.1021/ja027411v.
(a) P. Wasserscheid and T. Welton, Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, Germany (2003); (b) V. Jurčík and R. Wilhelm, Green Chem., 7, 844 (2005); doi:10.1039/b511062a.
S.P. Nolan, J. Am. Chem. Soc., 129, 8923 (2007); doi:10.1021/ja076926p.
F. Glorius, N-Heterocyclic Carbenes in Transition Metal Catalysis; Springer: Berlin (2007).
E.A.B. Kantchev, C.J. O’Brien and M.G. Organ, Angew. Chem. Int. Ed., 46, 2768 (2007); doi:10.1002/anie.200601663.
S. Würtz and F. Glorius, Acc. Chem. Res., 41, 1523 (2008); doi:10.1021/ar8000876.
S. Díez-González, N. Marion and S.P. Nolan, Chem. Rev., 109, 3612 (2009); doi:10.1021/cr900074m.
T. Droge and F. Glorius, Angew. Chem. Int. Ed., 49, 6940 (2010); doi:10.1002/anie.201001865.
A.J. Arduengo, Preparation of 1,3-Disubstituted Imidazolium Salts. U.S. Patent 5,077,414 (1991).
B. Krieg and G.Z. Manecke, Naturforsch, 22, 132 (1967).

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References

A.J. Arduengo, R.L. Harlow and M. Kline, J. Am. Chem. Soc., 113, 361 (1991); doi:10.1021/ja00001a054.

(a) F.E. Hahn and M.C. Jahnke, Angew. Chem. Int. Ed., 47, 3122 (2008); doi:10.1002/anie.200703883; (b) W.A. Herrmann, Angew. Chem. Int. Ed., 41, 1290 (2002); doi:10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y.

(a) F.E. Hahn, Angew. Chem. Int. Ed., 45, 1348 (2006); doi:10.1002/anie.200503858; (b) D. Bourissou, O. Guerret, F.P. Gabbai and G. Bertrand, Chem. Rev., 100, 39 (2000); doi:10.1021/cr940472u; (c) W.A. Herrmann and C. Kocher, Angew. Chem. Int. Ed. Engl., 36, 2162 (1997); doi:10.1002/anie.199721621.

V. Nair, S. Bindu and V. Sreekumar, Angew. Chem. Int. Ed., 43, 5130 (2004); doi:10.1002/anie.200301714.

(a) D. Enders, O. Niemeier and A. Henseler, Chem. Rev., 107, 5606 (2007); doi:10.1021/cr068372z; (b) N. Marion, S. Díez-González and S.P. Nolan, Angew. Chem. Int. Ed., 46, 2988 (2007); doi:10.1002/anie.200603380.

(a) L. Jafarpour and S.P. Nolan, Adv. Organomet. Chem., 46, 181 (2000); doi:10.1016/S0065-3055(00)46004-1; (b) W.A. Herrmann, T. Weskamp and V.P.W. Böhm, Adv. Organomet. Chem., 48, 1 (2001); doi:10.1016/S0065-3055(01)48001-4; (c) C.M. Crudden and D.P. Allen, Coord. Chem. Rev., 248, 2247 (2004); doi:10.1016/j.ccr.2004.05.013; (d) N.M. Scott and S.P. Nolan, Eur. J. Inorg. Chem., 1815 (2005); doi:10.1002/ejic.200500030; (e) J.C. Garrison and W.J. Youngs, Chem. Rev., 105, 3978 (2005); doi:10.1021/cr050004s; (f) V. Dragutan, I. Dragutan, L. Delaude and A. Demonceau, Coord. Chem. Rev., 251, 765 (2007); doi:10.1016/j.ccr.2006.09.002.

(a) D. Enders and T. Balensiefer, Acc. Chem. Res., 37, 534 (2004); doi:10.1021/ar030050j; (b) V. César, S. Bellemin-Laponnaz and L.H. Gade, Chem. Soc. Rev., 33, 619 (2004); doi:10.1039/b406802p.

A. Aidouni, S. Bendahou, A. Demonceau and L. Delaude, J. Comb. Chem., 10, 886 (2008); doi:10.1021/cc800101k.

P.I. Dalko and L. Moisan, Angew. Chem. Int. Ed., 43, 5138 (2004); doi:10.1002/anie.200400650.

V. Jurčík and R. Wilhelm, Org. Biomol. Chem., 3, 239 (2005); doi:10.1039/b415023f.

S. Jacobsen, P.H. Degee, H.G. Fritz, P.H. Dubois and R. Jerome, Polym. Eng. Sci., 39, 1311 (1999); doi:10.1002/pen.11518.

M.S. Kerr, J. Read de Alaniz and T. Rovis, J. Am. Chem. Soc., 124, 10298 (2002); doi:10.1021/ja027411v.

(a) P. Wasserscheid and T. Welton, Ionic Liquids in Synthesis; Wiley-VCH: Weinheim, Germany (2003); (b) V. Jurčík and R. Wilhelm, Green Chem., 7, 844 (2005); doi:10.1039/b511062a.

S.P. Nolan, J. Am. Chem. Soc., 129, 8923 (2007); doi:10.1021/ja076926p.

F. Glorius, N-Heterocyclic Carbenes in Transition Metal Catalysis; Springer: Berlin (2007).

E.A.B. Kantchev, C.J. O’Brien and M.G. Organ, Angew. Chem. Int. Ed., 46, 2768 (2007); doi:10.1002/anie.200601663.

S. Würtz and F. Glorius, Acc. Chem. Res., 41, 1523 (2008); doi:10.1021/ar8000876.

S. Díez-González, N. Marion and S.P. Nolan, Chem. Rev., 109, 3612 (2009); doi:10.1021/cr900074m.

T. Droge and F. Glorius, Angew. Chem. Int. Ed., 49, 6940 (2010); doi:10.1002/anie.201001865.

A.J. Arduengo, Preparation of 1,3-Disubstituted Imidazolium Salts. U.S. Patent 5,077,414 (1991).

B. Krieg and G.Z. Manecke, Naturforsch, 22, 132 (1967).

Author biographies is not available.

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