Suzuki-Miyaura cross-coupling reaction catalyzed using highly efficient CN-dimeric ortho-palladated complex under microwave irradiation and conventional heating
الموضوعات : Iranian Journal of Catalysis
Abdol Reza Hajipour
1
(
Pharmaceutical Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan, Iran.
)
Fatemeh Abrishami
2
(
Pharmaceutical Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan, Iran.
)
Fatemeh Rafiee
3
(
Department of Chemistry, Faculty of Science, Alzahra University, Vanak, Tehran, Iran.
)
الکلمات المفتاحية: 2-Methoxyphenethylamine, Ortho-palladated complex, Suzuki–Miyaura reaction, Aryl halide, Arylboronic acid,
ملخص المقالة :
Suzuki cross-coupling reaction of different aryl halides with arylboronic acids was successfully carried out in methanol using ortho-palladated complex of 2-methoxyphenethylamine. All substrates afforded the corresponding products in good to high yields in the presence of low amounts of this complex as efficient and active catalyst. Application of microwave irradiation improved the yields of the reactions and reduced the reaction times some extent in comparison with traditional heating conditions.
[1] H. Prokopcová, J. Ramírez, E. Fernández, C.O. Kappe, Tetrahedron Lett. 49 (2008) 4831-4835.
[2] E. Tas, A. Kilic, M. Durgun, I. Yilmaz, I. Ozdemir, N. Gurbuz, J. Organomet. Chem. 694 (2009) 446-454.
[3] a) N. Miyaura, A. Suzuki, Chem. Rev. 95 (1995) 2457-2483; b) A. Suzuki, J. Organomet. Chem. 576 (1999) 147-168; (c) A. Roucoux, J. Schulz, H. Patin, Chem. Rev. 102 (2002) 3757-3778; d) A. Suzuki, J. Organomet. Chem. 653 (2002) 83-90; e) N. Miyaura, Metal-catalyzed cross-coupling reactions, in: de Meijere, A., Diederich, F. (Eds.), Wiley-WCH: Weinheim, Germany, 1 (2004) 41–123; f) S. Ikegami, H. Hamamoto, Chem. Rev. 109 (2009) 583-593.
[4] F. Amoroso, S. Colussi, A. Del Zotto, J. Llorca, A. Trovarelli, Catal. Commun. 12 (2011) 563-567.
[5] H. Neumann, A. Brennführer, M. Beller, Chem. Eur. J. 14 (2008) 3645-3652.
[6] K. Asai, G. Konishi, K. Sumi, S. Kawauchi, Polym. Chem. 1 (2010) 321-325.
[7] C. Torborg, M. Beller, Adv. Synth. Catal. 351 (2009) 3027-3043.
[8] A.R. Siamaki, A.R.S. Khder, V. Abdelsayed, M.S. El-shall, B.F. Gupton, J. Catal. 279 (2011) 1-11.
[9] P. Das, C. Sarmah, A. Tairai, U. Bora, Appl. Organometal. Chem. 25 (2011) 283-288.
[10] D. Srimani, A. Sarkar, Tetrahedron Lett. 49 (2008) 6304-6307.
[11] H. Firouzabadi, N. Iranpoor, A. Ghaderi, M. Ghavami, S. J. Hoseini, Bull. Chem. Soc. Jpn. 84 (2011) 100-109.
[12] D. Zou, H. Cui, L. Qin, J. Li, Y. Wu, Synlett (2011) 349-356.
[13] M. Beller, H. Fischer, W. A. Herrmann, K. Öfele, C. Brossmer, Angew. Chem, Int. Ed. 34 (1995) 1844-1848.
[14] M. Genov, A. Almoln, P. Espinet, Tetrahedron: Asymmetry 18 (2007) 625-627.
[15] K.M. Dawood, Tetrahedron 63 (2007) 9642-9651.
[16] J. Lasri, T.C.O. Mac Leod, A.J.L. Pombeiro, Appl. Catal. A: Gen. 397 (2011) 94-102.
[17] C.O. Kappe, Angew. Chem. Int. Ed. 43 (2004) 6250-6284.
[18] M. Larhed, A. Hallberg, J. Org. Chem. 61 (1996) 9582-9584.
[19] M. Larhed, G. Lindeberg, A. Hallberg, Tetrahedron Lett. 37 (1996) 8219-8222.
[20] N.E. Leadbeater, M. Marco, Org. Lett. 4 (2002) 2973-2976.
[21] R.K. Arvela, N.E. Leadbeater, Org. Lett. 7 (2005) 2101-2104.
[22] N.E. Leadbeater, M. Marco, J. Org. Chem. 68 (2003) 888-892.
[23] R.K. Arvela, N.E. Leadbeater, M.S. Sangi, V.A. Williams, P. Granados, R.S. Singer, J. Org. Chem. 70 (2005) 161-168.
[24] R.K. Arvela, N.E. Leadbeater, T.M. Mack, C.M. Kormos, Tetrahedron Lett. 47 (2006) 217-220.
[25] R.K. Arvela, N.E. Leadbeater, M.J. Collins, Tetrahedron 61 (2005) 9349-9355.
[26] N.E. Leadbeater, V.A. Williams, T.M. Barnard, M. Collins, Org. Process Res. Dev. 10 (2006) 833-837.
[27] F. Chanthavong, N.E. Leadbeater, Tetrahedron Lett. 47 (2005) 1909-1912.
[28] K.B. Avery, W.G. Devine, C.M. Kormos, N.E. Leadbeater, Tetrahedron Lett. 51 (2009) 2851-2853.
[29] N.E. Leadbeater, Chem. Commun. (2005) 2881-2902.
[30] A.R. Hajipour, F. Abrishami, G. Tavakoli, Trans. Met. Chem. 36 (2011) 725-730.
[31] A.R. Hajipour, K. Karami, A. Pirisedigh, Inorg. Chim. Acta, 370 (2011) 531-535.
[32] A.R. Hajipour, K. Karami, A. Pirisedigh, J. Organomet. Chem. 694 (2009) 2548-2554.
[33] A.R. Hajipour, K. Karami, A. Pirisedigh, Appl. Organomet. Chem. 23 (2009) 504-511.
[34] A.R. Hajipour, K. Karami, G. Tavakoli, Appl. Organomet. Chem. 24 (2010) 798-804.
[35] A.R. Hajipour, K. Karami, A. Pirisedigh, Appl. Organomet. Chem. 24 (2010) 454-457.
[36] A.R. Hajipour, K. Karami, G. Tavakoli, A. Pirisedigh, J. Organomet. Chem. 96 (2011) 819-824.
[37] B. Mu, T. Li, J. Li, Y. Wu, J. Organomet. Chem. 693 (2008) 1243-1251.
[38] A.F. Littke, G.C. Fu, Angew. Chem. Int. Ed. 37 (1999) 3387-3388.
[39] S.E. Denmark, M.H. Ober, Org. Lett. 5 (2003) 1357-1360.
[40] K. Karami, C. Rizzoli, M. Mohamadi Salah, J. Organomet. Chem. 696 (2011) 940-945.
[41] H.J. Lehmler, L.W. Robertson, Chemosphere 45 (2001), 137-143.
[42] A. Kamal, K. Sreekanth, P. P. Kumar, G. Balakishan, M.G. Ramaiah, M. Janaki, S.N.C.V.L. Pushpavalli, P. Ray, M. Pal Bhadra, Eur. J. Med. Chem. 45 (2010) 2173-2181.
[43] Y. Kitamura, A. Sakurai, T. Udzu, T. Maegawa, Y. Monguchi, H. Sajiki, Tetrahedron 63 (2007) 10596-10602.
[44] J.H. Li, Q.M. Zhu, Y.X. Xie, Tetrahedron 62 (2006) 10888-10895.
[45] A.R. Hajipour, I. Mahboobi Dehbane, F. Rafiee, Appl. Organometal. Chem. 26 (2012) 743–747.
[46] F. Durap, M. Rakap, M. Aydemir, S. Özkar, Appl. Catal. A: Gen. 382 (2010) 339-344.
