Abstract
Ionic liquids (ILs) are more and more suggested as substitutes for traditional solvents in organic synthesis and catalysis. They are suitable candidates for the dissolution of ionic complexes. They can activate and retain them in a polar state: in fact, they act as sequestrands, opening the route to two-phase processes and easier catalyst recovery. This paper reviews authors' results with the development of new syntheses of ILs and applications in carbon–carbon bond formation (dimerisation of methyl acrylate) and redistribution (ring closing metathesis) reactions using ionic precatalysts.
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References
W. Keim, New J. Chem. 11 (1987) 531and references therein.
B. Cornils, W.A. Herrmann and R.W. Eckl, J. Mol Catal. A: Chemical 116 (1997) 27, and references therein.
E. Kuntz, CHEMTECH 17 (1987) 570.
Applied Homogeneous Catalysis with Organometallic Compounds, 2nd edn, Vol. 2, eds. B. Cornils and W.A. Herrmann (Wiley-VCH, Weinheim, 2002, ch. 3.1.1.
J.D. Holbrey and K.R. Seddon, Clean Prod. Processes 1 (1999) 223.
See for examples, (a) Ionic Liquids: Industrial Applications for Green Chemistry, eds. R.D. Rogers and K.R. Seddon, ACS Symposium Series 818 (American Chemical Society, Washington DC, 2002), and (b) the special issue of Green Chemistry, 4 (2002) 73-180.
T. Welton, Chem. Rev. 99 (1999) 2071.(b)P. Wasserscheid and W. Keim, Angew. Chem., Internat. Ed. Engl. 39 (2000) 3772.(c)R.A. Sheldon, Chem. Commun. (2001) 2399; (d)C.M. Gordon, Appl. Catal. A: General 222 (2001) 101. (e)J. Dupont, R.F. de Souza and P.A.Z. Suarez, Chem. Rev. 102 (2002) 3667.
A. Bösmann, G. Franciò, E. Janssen, M. Solinas, W. Leitner and P. Wasserscheid, Angew.Chem, Int. Ed. Engl. 40 (2001) 2697.
P.A.Z. Suarez, S. Einloft, J.E.L. Dullius, R.F. de Souza and J. Dupont, Polyhedron 15 (1996) 1217.
A.-A. Shaik and S. Siravam, Chem. Rev. 96 (1996) 951. P. Tundo and M. Selva, Acc. Chem. Res. 35 (2002) 706.
S. Mori, K. Ida and M. Ue, US Pat. 4,892,944 (Mitsubishi, 1990).
B. Albert and M. Jansen, Z. Anorg. Allg. Chem. 621 (1995) 1735.
M. Lissel, S. Schmidt and B. Neumann, Synthesis (1986) 382.(b)M. Lissel, Liebig. Ann.Chem. (1987) 77.
M. Ue, M. Takeda, T. Takahashi and M. Takehara, US Pat. 5,856,513 (Mitsubishi, 2000).
M. Ue, M. Tekeda, T. Takahashi and M. Takehara, Electrochem. Solid-State Lett. 5 (2002) A119.
J. Fischer, W. Siegel, V. Bomm, M. Fischer and K. Mundinger, US Pat. 6,175,019 (BASF, 2001).
D. Poinsot, I. Tkatchenko and I. Tommasi, French Demande 02 12 692 (Université de Bourgogne, 2002).
J.D. Holbrey, W.M. Reichert, I. Tkatchenko, E. Bouajila, O. Walter, I. Tommasi and R.D. Rogers, Chem. Commun. (2003) 29.
E. Bouajila, H. Chermette, D. Poinsot, I. Tkatchenko, I. Tommasi and O. Walter, submitted.
E. Bouajila and I. Tkatchenko, unpublished results.
B.M. Trost, Chem. Eur. J. 4 (1998) 2405.
J. Zimmermann, P. Wasserscheid, I. Tkatchenko and S. Stutzmann, Chem. Commun. (2002) 760.
Christie, S. Subramanian, L. Wang and M.J. Zaworotko, Inorg. Chem. 32 (1993) 5415.(b) J.D. Holbrey and;K.R. Seddon, J. Chem.Soc., Dalton Trans. (1999) 2133.
C.K. Lee, H.W. Hunagn and I.J.N. Liri, J. Chem. Soc., Chem. Commun. (2000) 1911.
K.K. Laali and V.J. Gettwert, J. Org. Chem. 66 (2001) 35.
H. Ohno and M. Yoshizawa, Solid State Ionics 154–155 (2002) 303.
M. Picquet, I. Tkatchenko, I. Tommasi, P. Wasserscheid and J. Zimmermann, Adv. Synth. Catal. 345 (2003) in press.
M. Brookhart and S. Sabo-Etienne, J. Am. Chem. Soc. 113 (1991) 2777.(b) M. Brookhart and E. Hauptman, J. Am. Chem. Soc. 114 (1992) 4437.
I. Guibert, D. Neibecker and I. Tkatchenko, J. Chem. Soc., Chem. Commun. (1989) 1850.
P. Grenouillet, D. Neibecker and I. Tkatchenko, French Pat. 2,596,390 (Rhône-Poulenc, 1987).(b) P. Grenouillet, D. Neibecker and I. Tkatchenko, US Pat. 4,889,949 (Rhône-Poulenc, 1989).
M. Bonnet, L. Carmona, P. Grenouillet, I. Guibert, D. Neibecker and I. Tkatchenko, submitted.
D.S. McGuiness, K.J. Cavell, B.F. Yates, B.W. Skelton and A.H. White, J. Am. Chem. Soc. 123 (2001) 8317.
S. Gründemann, M. Albrecht, A. Kovacevic, J.W. Faller and R.H. Crabtree, J. Chem. Soc., Dalton Trans. (2002) 2163.
M. Picquet, S. Stutzmann, I. Tkatchenko, I. Tommasi, P. Wasserscheid and J. Zimmermann, Green Chemistry 5 (2003) 153.
I. Guibert, Thèse de doctoral de l'Université Paul Sabatier, Toulouse, 1986.
J. Zimmermann, I. Tkatchenko and P. Wasserscheid, Advan. Synth. Catal. 345 (2003) 402.
M.S. Sanford, L.H. Henling and R.H. Grubbs, Organometallic 17 (1998) 5384.
A. Fürstner, M. Liebl, C.W. Lehmann, M. Picquet, R. Kunz, C. Bruneau and P.H. Dixneuf, Chem. Eur. J. 6 (2000) 1847.
D. Sémeril, H. Olivier-Bourbigou, C. Bruneau and P.H. Dixneuf, Chem. Commun. (2002) 146.
See for example: Applied Homogeneous Catalysis with Organometallic Compounds, 2nd edn, eds. B. Cornils and W.A. Herrmann (Wiley-VCH, Weinheim, 2002).
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Picquet, M., Poinsot, D., Stutzmann, S. et al. Ionic Liquids: Media for Better Molecular Catalysis. Topics in Catalysis 29, 139–143 (2004). https://doi.org/10.1023/B:TOCA.0000029796.11969.ec
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DOI: https://doi.org/10.1023/B:TOCA.0000029796.11969.ec