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Cinnamic Acid Derivatives via Heck Reaction in an Aqueous- Biphasic Catalytic System with Easy Catalyst-Product Separation
Corresponding Author(s) : S.V. Jagtap
Asian Journal of Chemistry,
Vol. 25 No. 15 (2013): Vol 25 Issue 15
Abstract
A true biphasic [aqueous-organic] system for the coupling of water soluble sodium acrylate with different aryl halides for the synthesis of cinnamic acid derivatives has been developed, employing palladium catalysts that is soluble in organic phase. Amongst them, palladacycle was found to be stable in presence of water and could be recycled for four times with no loss in the activity. Such a system facilitates easy recycle of catalyst and also the removal of the salts from the catalyst phase, ensuring high activity with respect to cumulative turn over number (TON) and turn over frequency (TOF). The reaction was facilitated by organic as well as inorganic bases. The efficiency of the catalyst, role of organic/inorganic bases on the activity is reported.
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References
G.W. Parshall, Homogeneous Catalysis, Wiley Interscience, New York (1980).
E.G. Kuntz, Chemtech, 17, 570 (1987).
B.M. Bhanage and M. Arai, Catal. Rev., 43, 315 (2001).
W.A. Herrmann, C. Brossmer, K. Ofele, C.-P. Reisinger, T. Priermeir, M. Beller and H. Fischer, Angew. Chem. Int. Ed., 34, 1844 (1995).
W.A. Herrmann, C. Brossmer, C.-P. Reisinger, T.H. Riermeier, K. Ofele and M. Beller, Chem. Eur. J., 3, 1357 (1997).
B.M. Bhanage, F.G. Zhao, M. Shirai and M. Arai, Tetrahedron Lett., 39, 9509 (1998).
M. Beller, J.G.E. Krauter and A. Zapf, Angew. Chem. Int. Ed., 36, 772 (1997).
T. Thorpe, S.M. Brown, J. Crosby, S. Fitzjohn, J.P. Muxworthy and J. M.J. Williams, Tetrahedron Lett., 41, 4503 (2000).
R.B. DeVasher, L.R. Moore and K.H. Shaughnessy, J. Org. Chem., 69, 7919 (2004).
D.B.G. Williams, H. Lombard and C.W. Holzapfel, Synth. Commun., 31, 2077 (2001).
S.V. Jagtap and R.M. Deshpande, Catal. Today, 131, 353 (2008).
N.A. Bumagin, P.G. More and I.P. Beletskaya, J. Organomet. Chem., 371, 397 (1989).
A.C. Casalnuovo and J.C. Calabrese, J. Am. Chem. Soc., 112, 4324 (1990).
J.P. Genet, E. Blart and M. Savignac, Synlett, 715 (1992).
T. Jeffery, Tetrahedron Lett., 35, 3051 (1994).
J.P. Genet and M. Savignac, J. Organomet. Chem., 576, 305 (1999).
F.E. Herkes, A. Eisenstadt, Catalysis of Organic Reactions, Marcel Dekker, New York, p. 415 (1998)
O. Arrad and Y. Sasson, J. Am. Chem. Soc., 110, 185 (1988).
E.V. Dehmlow and S.S. Dehmlow, Phase Transfer Catalysis, VCH, Weinheim, New York and references cited, edn. 3 (1993).
I.P. Beletskaya and A.V. Cheprakov, Chem. Rev., 100, 3009 (2000).
D. Garbe, W. Gerhartz, J.S. Yamamoto, I.T. Campbell, R. Pfefferkorn and J.F Rounsville, Ullmann’s Encyclopaedia of Industrial Chemistry, Vol. A7, 99, VCH: Weinheim (1992).
F. Natella, M. Nardini, M. Di Felice and C. Scaccini, J. Agric. Food Chem., 47, 1453 (1999).
S. Adisakwattana, K. Sookkongwaree, S. Roengsumran, A. Petsom, N. Ngamrojnavanich, W. Chavasiri, S. Deesamer and S. Yibchok-anun, Bioorg. Med. Chem. Lett., 14, 2893 (2004).
B.J. McCormick, E.N. Jaynes Jr. and R.I. Kaplan, Inorg. Synth., 13, 216 (1972).
S. Komiya, Synthesis of Organometallic Compounds-A Practical Guide (1997).
W.A. Herrmann, V.P.W. Bohm and C.-P. Reisinger, J. Organomet. Chem., 576, 23 (1999).
C.S. Consorti, M.L. Zanini, S. Leal, G. Ebeling and J. Dupont, Org. Lett., 5, 983 (2003).
I.P. Beletskaya and A.V. Cheprakov, J. Organomet. Chem., 689, 4055 (2004).
W.A. Herrmann, K.O¨fele, D.V. Preysing and S.K. Schneider, J. Organomet. Chem, 687, 229 (2003).