Synthesis of functionalized aryl-alkenes catalyzed by CN-ortho-palladated complex of 2,3-dimethoxybenzaldehyde oxime under microwave irradiation
الموضوعات : Iranian Journal of CatalysisFatemeh Rafiee 1 , Abdol Reza Hajipour 2
1 - Department of Chemistry, Faculty of Science, Alzahra University, Vanak, Tehran, Iran, email: f.rafiee@alzahra.ac.ir
2 - Pharmaceutical Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan 84156, IR Iran
الکلمات المفتاحية: Microwave irradiation, Heck reaction, ortho-Palladated catalyst, Oxime palladacycle complexes,
ملخص المقالة :
A new dimeric orthopalladated complex was synthesized via reaction of 2,3-dimethoxy benzaldehyde oxime with palladium chloride and lithium chloride in methanol as solvent and sodium acetate as base at room temperature. The catalytic activity of this dimeric [Pd{C6H2(-CH=NOH)-(OMe)2-2,3}(µ-Cl)]2 complex as an efficient, air, and moisture tolerant catalyst was investigated in Mizoroki–Heck cross coupling reaction of various aryl halides and also arenesulfonyl chloridesas the electrophilic partners with different coupling partner alkenes such as methylacrylate, methylmetacrylate and styrene . The combination of homogenous metal catalyst, microwave irradiation, and microwave-active polar solvents gave high yields of functionalized aryl-alkene products in short reaction times.
[1] J. Tsuji, Palladium Reagents and Catalysts: Innovations in Organic Synthesis, Wiley, Chichester, 1995.
[2] B.C.G. Soederberg, Coord. Chem. Rev. 241 (2003) 147-247.
[3] S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 58 (2002) 9633-9695.
[4] F. Alonso, I.P. Beletskaya, M. Yus, Tetrahedron 64 (2008) 3047-3101.
[5] L.H. Pignolet, Homogeneous Catalysis with Metal Phosphine Complexes, Plenum, New York, 1983.
[6] M. Feuerstein, H. Doucet, M. Santelli, J. Mol. Catal. A: Chem. 256 (2006) 75-84.
[7] F.N. Ngassa, E.A. Lindsey, B.E. Haines, Tetrahedron 65 (2009) 4085-4091.
[8] K. Prabakaran, F.N. Khan, J.S. Jin, Tetrahedron Lett. 52 (2011) 2566-2570.
[9] C. Yang, S.P. Nolan, Organometallics 21 (2002) 1020-1023.
[10] M. Eckhanlt, G.C. Fu, J. Am. Chem. Soc. 125 (2003) 13642-13643.
[11] J.H. Kim, D.H. Lee, B.H. Jun, Y.S. Lee, Tetrahedron Lett. 48 (2007) 7079-7084.
[12] J. Buey, P. Espinet, J. Organomet. Chem. 507 (1996) 137-145.
[13] K.K. Lo, C. Chung, T.K. Lee, L. Lui, K.H. Tang, N. Zhu, Inorg. Chem. 42 (2003) 6886-6897.
[14] C. Lopez, A. Caubet, S. Perez, X. Solans, M. Font-Bardía, J. Organomet. Chem. 681 (2003) 82-90.
[15] R.B. Bedford, L.T. Pilarski, Tetrahedron Lett. 49 (2008) 4216-4219.
[16] A. Zapf, M. Beller, Top. Catal. 19 (2002) 101-109.
[17] S. Bong Park, H. Alper, Org. Lett. 5 (2003) 3209-3212.
[18] I.P. Beletskaya, A.V. Cheprakov, Chem. Rev. 100 (2000) 3009-3066.
[19] A.B. Dounay, L.E. Overman, Chem. Rev. 103 (2003) 2945-2964.
[20] M. Li, R. Hua, Appl Organometal Chem 22 (2008) 397-401.
[21] B.K. Singh, N. Kaval, S. Tomar, E.V. Eycken, V.S. Parmar, Org. Process Res. Dev. 12 (2008) 468-474.
[22] K.S.A. Vallin, P. Emilsson, M. Larhed, A. Hallberg, J. Org. Chem. 67 (2002) 6243-6246.
[23] C.O. Kappe, Angew. Chem. Int. Ed. 43 (2004) 6250-6284.
[24] A.R. Hajipour, F. Rafiee, Tetrahedron Lett. 52 (2011) 4782-4787.
[25] A.R. Hajipour, F. Rafiee, Appl. Organomet. Chem. 25 (2011) 542-551.
[26] A.R. Hajipour, F. Rafiee, A.E. Ruoho, J. Iran. Chem. Soc. 7 (2010) 114-118.
[27] A.R. Hajipour, F. Abrishami, Iran. J. Catal. 2 (2012) 95-100.
[28] A.R. Hajipour, K. Karami, A. Pirisedigh, J. Organomet. Chem. 694 (2009) 2548-2554.
[29] A.R. Hajipour, K. Karami, A. Pirisedigh, Appl. Organometal. Chem. 23 (2009) 504-511.
[30] A.R. Hajipour, K. Karami, Gh. Tavakoli, Appl. Organometal. Chem. 24 (2010) 798-804.
[31] Q. Yao, E.P. Kinney, Z. Yang, J. Org. Chem. 68 (2003) 7528-7531.
[32] X. Cui, Z. Li, C.Z. Tao, Y. Xu, J. Li, L. Liu, Q.X. Guo, Org. Lett. 8 (2006) 2467-2470.
[33] Y. Fuchita, K. Yoshinaga, T. Hanaki, H. Kawano, J. Kinoshita-Nagaoka, J. Organomet. Chem. 580 (1999) 273-281.
[34] S.B. Atla, A.A. Kelkar, V.G. Puranik, W. Bensch, R.V. Chaudhari, J. Organomet. Chem. 694 (2009) 683-690.
[35] M.R. Eberhard, Org. Lett. 6 (2004) 2125-2128.
[36] D.E. Bergbreiter, P.L. Osburn, J.D. Frels, Adv. Synth. Catal. 347 (2004) 172-184.
[37] L. Djakovitch, K. Kçhler, J.G. de Vries, in: D. Astruc (Ed.), Nanoparticles and Catalysis, Wiley-VCH, Weinheim, 2008, pp 303-348.
[38] M.T. Reetz, E. Westermann, Angew. Chem. Int. Ed. 39 (2000) 165-168.
[39] N. Iranpoor, H. Firouzabadi, R. Azadi, Eur. J. Org. Chem. (2007) 2197–2201.
[40] N.J. Whitcomb, K.K. Hill, S.E. Gibson, Tetrahedron 57 (2001) 7449-7476.
[41] G.D. Frey, J. Schütz, E. Herdtweck, W.A. Herrmann, Organometallics 24 (2005) 4416-4426.