Application of dimeric ortho-palladated complex of 2-methoxyphenethylamine in the Heck coupling reaction

Authors

1 Pharmaceutical Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran. Department of Pharmacology, University of Wisconsin, Medical School, 1300 University Avenue, Madison, 53706-1532, WI, USA

2 Pharmaceutical Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran.

Abstract

The application of the [Pd{C6H3(CH2CH2NH2)-4-OMe-5-κ2-C,N}(μ-Br)]2 complex of 2-methoxyphenethylamine in the Heck coupling reaction was considered under both conventional and microwave irradiation conditions, and their results were compared. This complex is an efficient, stable and non-sensitive to air and moisture catalyst for the vinylation of substituted aryl halides with different electronic properties. The cross-coupled products were produced in good to excellent yields using a catalytic amount of this complex in N-methyl-2-pyrrolidone (NMP) at 130 °C. In comparison to conventional heating conditions, the reactions under microwave irradiation gave higher yields in shorter reaction times.

Keywords


[1] K.C. Nicolaou, P.G. Bulger, D. Sarlah, Angew. Chem. Int. Ed. Engl. 44 (2005) 4442-4489.

[2] M.S. Schiedel, C.A. Briehn, P. Bäuerle, J. Organomet. Chem. 653 (2002) 200-208.

[3] V.T. Trepohl; M. Oestreich, Modern Arylation Methods, Wiley-VCH: Weinheim, 2009.

[4] M.R. Shaaban, A.F.  Darweesh, K.M.  Dawood, A.M. Farag, ARKIVOC (x) (2010) 208-225.

[5] A.F. Littke, G.C. Fu, Angew. Chem. Int. Ed. Engl. 41 (2002) 4176-4211.

[6] R.F. Heck, J. Am. Chem. Soc. 90 (1968) 5518-5526.

[7] B. Cornils, W.A. Herrmann, Applied homogeneous catalysis with organometallic compounds, Wiley-VCH: Weinheim., 2002.

[8] J.P. Knowles, A. Whiting, Org. Biomol. Chem. 5 (2007) 31-44.

[9] A. de Meijere, F.E. Meyer, Angew. Chem. Int. Ed. Engl. 33 (1994) 2379-2411.

[10] W. Cabri, I. Candiani, Acc. Chem. Res. 28 (1995) 2-7.

[11] C. Amatore, A. Jutand, Acc. Chem. Res. 33 (2000) 314-321.

[12] M. Li, R. Hua, Appl. Organomet. Chem. 22 (2008) 397-401.

[13] L.F. Tietze, W. Buhr, Angew. Chem. Int. Ed. Engl. 34 (1995) 1366-1368.

[14] M. Beller, A. Zapf, Synlett (1998) 792-793.

[15] M. Julia, M. Duteil, C. Grard, E. Kuntz, Bull. Soc. Chim. Fr. (1973) 2791-2794.

[16] M.T. Reetz, R. Breinbauer, K. Wanninger, Tetrahedron Lett. 37 (1996) 4499-4502.

[17] W.A. Herrmann, C.P. Reisinger, M. Spiegler, J. Organomet. Chem. 572 (1998) 93-98.

[18] A. Gonzalez, C. Lopez, X. Solans, M. Font-Bardia, E. Molins, J. Organomet. Chem. 693 (2008) 2119-2131.

[19] G.M. Lobmaier, G.D. Frey, R.D. Dewhurst, E. Herdtweck, W.A. Herrmann, Organometallics 26 (2007) 6290-6299.

[20] G.D. Frey, J. Schütz, E. Herdtweck, W.A. Herrmann, Organometallics 24 (2005) 4416-4426.

[21] W.A. Herrmann, K. Öfele, D.V. Preysing, S.K. Schneider, J. Organomet. Chem. 687 (2003) 229-248.

[22] G.D. Frey, W.A. Herrmann, J. Organomet. Chem. 690 (2005) 5876-5880.

[23] a) G.A. Grasa, S.P. Nolan, Org. Lett. 3 (2001) 119-120; b) H. Tang, K. Menzel, G.C. Fu, Angew. Chem., Int. Ed. Engl. 42 (2003) 5079-5082.

[24] L.H. Pignolet, Homogeneous catalysis with metal phosphine complexes, Plenum: New York, 1983.

[25] C.O. Kappe, A. Stadler, Microwave in organic and medicinal chemistry, Wiley-VCH, Weinhiem, 2005, b) C.O. Kappe, Angew. Chem. Int. Ed. Engl. 43 (2004) 6250-6284.

[26] A. Loupy, Microwaves in organic synthesis; Wiley-VCH, Weinheim, 2006.

[27] A.R. Hajipour, F. Abrishami, G. Tavakoli, Transition Met. Chem. 36 (2011) 725-730.

[28] A.R. Hajipour, K. Karami, A. Pirisedigh, Inorg. Chim. Acta 370 (2011) 531-535.

[29] A.R. Hajipour, K. Karami, A. Pirisedigh, A.E. Ruoho, Amino Acids 37 (2009) 537-541.

[30] A.R. Hajipour, K. Karami, G.Tavakoli, Appl. Organomet. Chem. 25 (2011) 567-576.

[31] A.R. Hajipour, K. Karami, A. Pirisedigh, A.E. Ruoho, J. Organomet. Chem. 694 (2009) 2548-2554.

[32] A.R. Hajipour, K. Karami, A. Pirisedigh, Appl. Organomet. Chem. 23 (2009) 504-511.

[33] A. El-Batta, C. Jiang, W. Zhao, R. Anness, A.L. Cooksy, M. Bergdahl, J. Org. Chem. 72 (2007) 5244-5259.

[34] R. Imashiro, M. Seki, J. Org. Chem. 69 (2004) 4216-4226.

[35] J. Bietz, H. Ritter, Macromol. Chem. Phys. 21 (2009) 1114-1119.

[36] R. Cella, H.A. Stefani, Tetrahedron 62 (2006) 5656-5662.

[37] E. Artuso, M. Barbero, I. Degani, S. Dughera, R. Fochi, Tetrahedron 62 (2006) 3146-3157.

[38] A.R. Hajipour, K. Karami, G.Tavakoli, Appl. Organometal. Chem. 24 (2010) 798–804.

[39] N.J. Whitcomb, K.K. Hill, S.E. Gibson, Tetrahedron 57 (2001) 7449-7476.

[40] N. Iranpoor, H. Firouzabadi, R. Azadi, Eur. J. Org. Chem. (2007) 2197–2201.

[41] A. Slamani, S. Demir, S. Özdemir, Catal. Commun. 29 (2012) 141-144.