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Silica Sulfuric Acid-Catalyzed One-Pot Synthesis of 1,3-Diarylimidazolium Tetrafluoroborate
Corresponding Author(s) : Yu Wan
Asian Journal of Chemistry,
Vol. 27 No. 8 (2015): Vol 27 Issue 8
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.
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- A.J. Arduengo, R.L. Harlow and M. Kline, J. Am. Chem. Soc., 113, 361 (1991); doi:10.1021/ja00001a054.
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- V. Nair, S. Bindu and V. Sreekumar, Angew. Chem. Int. Ed., 43, 5130 (2004); doi:10.1002/anie.200301714.
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- A. Aidouni, S. Bendahou, A. Demonceau and L. Delaude, J. Comb. Chem., 10, 886 (2008); doi:10.1021/cc800101k.
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- V. Jurčík and R. Wilhelm, Org. Biomol. Chem., 3, 239 (2005); doi:10.1039/b415023f.
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- 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).
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).