Ligand-free heck coupling and homocoupling of aryl halides in the presence of tetrabutylammonium nitrate

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• 作者：Najmeh Nowrouzi ; Dariush Tarokh
• 关键词：Heck reaction ; Homocoupling reaction ; Ligand free ; Palladium ; Tetrabutylammonium nitrate
• 刊名：Journal of the Iranian Chemical Society
• 出版年：2015
• 出版时间：September 2015
• 年：2015
• 卷：12
• 期：9
• 页码：1623-1628
• 全文大小：573 KB
• 参考文献：1.S. Brase, A. de Meijere, Metal-catalyzed cross-coupling reactions, in Diederich F, ed. by P.J. Stang (Wiley, Weinheim, 1998), pp. 99鈥?66
  2.A.F. Littke, G.C. Fu, Angew. Chem. Int. Ed. 41, 4176鈥?211 (2002)View Article
  3.I.P. Beletskaya, A.V. Cheprakov, Chem. Rev. 100, 3009鈥?066 (2000)View Article
  4.N. Miyaura, A. Suzuki, Chem. Rev. 95, 2457鈥?483 (1995)View Article
  5.N. Nowrouzi, D. Tarokh, S. Motevalli, J. Mol. Catal. A: Chem. 385, 13鈥?7 (2014)View Article
  6.I. Nakamura, Y. Yamamoto, Chem. Rev. 104, 2127鈥?198 (2004)View Article
  7.N. Iranpoor, H. Firouzabadi, S. Motevalli, M. Talebi, J. Organomet. Chem. 708鈥?09, 118鈥?24 (2012)View Article
  8.N. Iranpoor, H. Firouzabadi, S. Motevalli, J. Mol. Catal. A: Chem. 355, 69鈥?4 (2012)View Article
  9.H. Firouzabadi, N. Iranpoor, M. Gholinejad, J. Organomet. Chem. 695, 2093鈥?097 (2010)View Article
  10.L.H. Pignolet, Homogeneous catalysis with metal phosphine complexes (Plenum, New York, 1983)View Article
  11.G.W. Parshall, S. Ittel, Homogeneous catalysis (Wiley, New York, 1992)
  12.J.P. Collman, L.S. Hegedus, J.R. Norton, R.G. Finke, Principles and applications of organotransition metal chemistry (University Science, Mill Valley, 1987)
  13.N. Iranpoor, H. Firouzabadi, Y. Ahmadi, Eur. J. Org. Chem. (2), 305鈥?11 (2012)
  14.Z.D. Petrovic, D. Simijonovic, V.P. Petrovic, S. Markovic, J. Mol. Catal. A Chem. 327, 45鈥?0 (2010)View Article
  15.J.H. Li, W.J. Liu, Y.X. Xie, J. Org. Chem. 70, 5409鈥?412 (2005)View Article
  16.J.H. Li, X.C. Hu, Y. Liang, Y.X. Xie, Tetrahedron 62, 31鈥?8 (2006)View Article
  17.B.K. Allam, K.N. Singh, Synthesis 7, 1125鈥?131 (2011)
  18.M.T. Reetz, E. Westermann, Angew. Chem. Int. Ed. 39, 165鈥?68 (2000)View Article
  19.M. T. Reetz, J. G. de Vries, Chem. Commun. (14), 1559鈥?563 (2004)
  20.T. Jeffery, J. Chem. Soc. Chem. Commun. (19), 1287鈥?289 (1984)
  21.M.T. Reetz, M. Maase, Adv. Mater. 11, 773鈥?77 (1999)View Article
  22.G. Battistuzzi, S. Cacchi, G. Fabrizi, Synlett (3), 439鈥?42 (2002)
  23.D. E. Kaufmann, M. Nouroozian, H. Henze, Synlett (11), 1091鈥?092 (1996)
  24.M.T. Reetz, W. Helbig, S.A. Quaiser, U. Stimming, N. Breuer, R. Vogel, Science 267, 367鈥?69 (1995)View Article
  25.M.T. Reetz, M. Winter, R. Breinbauer, T. Thurn-Albrecht, W. Vogel, Chem. Eur. J. 7, 1084鈥?094 (2001)View Article
  26.T. Jeffery, Tetrahedron 52, 10113鈥?0130 (1996)View Article
  27.W.M. Seganish, M.E. Mowery, S. Riggleman, P. DeShong, Tetrahedron 61, 2117鈥?121 (2005)View Article
  28.H.S. He, C. Zhang, C.K.W. Ng, P. Toy, H. Tetrahedron 61, 12053鈥?2057 (2005)View Article
  29.N. Ma, Z. Duan, Y. Wu, J. Organomet. Chem. 691, 5697鈥?700 (2006)View Article
  30.J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 102, 1359鈥?469 (2002)View Article
  31.M. Tieco, L. Testaferri, M. Tingoli, D. Chianelli, M. Montanucci, Synthesis (9), 736鈥?38 (1984)
  32.A. Yanagisawa, H. Hibino, S. Habaue, Y. Hisada, H. Yamamato, J. Org. Chem. 57, 6386鈥?387 (1992)View Article
  33.B.C. Rann, P. Dutta, A. Sarkar, Tetrahedron Lett. 39, 9557鈥?558 (1998)View Article
  34.K. Abiraj, G.R. Srinivasa, D.C. Gowda, Tetrahedron Lett. 45, 2081鈥?084 (2004)View Article
  35.C. Qi, X. Sun, C. Lu, J. Yang, Y. Du, H. Wu, X.M. Zhang, J. Organomet. Chem. 694, 2912鈥?916 (2009)View Article
  36.P. Sun, Y. Zhu, H. Yang, H. Yan, L. Lu, X. Zhang, J. Mao, Org. Biomol. Chem. 10, 4512鈥?515 (2012)View Article
  37.H. Firouzabadi, N. Iranpoor, A. Ghaderi, J. Mol. Cat. A Chem. 347, 38鈥?5 (2011)View Article
  38.J. Zou, K.S. Iyer, S.G. Stewart, C.L. Raston, New J. Chem. 35, 854鈥?60 (2011)View Article
  39.H.S. He, C. Zhang, N.G. Ka-Wo, P.H. Toy, Tetrahedron 61, 12053鈥?2057 (2005)View Article
  
• 作者单位：Najmeh Nowrouzi (1)
  Dariush Tarokh (1)
  
  1. Department of Chemistry, Faculty of Sciences, Persian Gulf University, 75169, Bushehr, Iran
  
• 刊物主题：Analytical Chemistry; Inorganic Chemistry; Physical Chemistry; Biochemistry, general; Organic Chemistry;
• 出版者：Springer Berlin Heidelberg
• ISSN：1735-2428

文摘

Tetrabutylammonium nitrate is reported as an effective reusable medium, suitable reducing and stabilizing agent for the Heck coupling reaction of aryl iodides and bromides with styrene and n-butyl acrylate. The efficient phosphine-free, palladium-catalyzed homocoupling reaction of aryl iodides and bromides is also demonstrated in the presence of tetrabutylammonium nitrate. The ionic liquid, still containing Pd (0) complex, is easily recovered and reused in several runs without losing its efficiency.