We have developed a simple and effective method for the activation of palladium phosphine complexes in the Suzuki reaction (TON up to 9800, TOF up to 58800 h-1) by selecting an aqueous reaction medium instead of organic solvents. This method was elaborated for a high yield synthesis of heteroaromatic biaryls with furyl and thienyl groups.
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References
A. Suzuki and Y. Yamamoto, Chem. Lett., 40, 894 (2011).
T. Kinzel, Y. Zhang, and S. L. Buchwald, J. Am. Chem. Soc., 132, 14073 (2010).
V. Pomel, J. Klicic, D. Covini, D. D. Church, J. P. Shaw, K. Roulin, F. Burgat-Charvillon, D. Valognes, M. Camps, C. Chabert, C. Gillieron, B. Françon, D. Perrin, D. Leroy, D. Gretener, A. Nichols, P. A. Vitte, S. Carboni, C. Rommel, M. K. Schwarz, and T. Rückle, J. Med. Chem., 49 , 3857 (2006).
P. Villain-Guillot, M. Gualtieri, L. Bastide, F, Roquet, J. Martinez, M. Amblard, M. Pugniere, and J. P. Leonetti, J. Med. Chem., 50, 4195 (2007).
A. R. Katritzky, S. R. Tala, H. Lu, A. V. Vakulenko, Q.-Y. Chen, J. Sivapackiam, K. Pandya, S. Jiang, and A. K. Debnath, J. Med. Chem., 52, 7631 (2009).
B. E. Sleebs, W. J. A. Kersten, S. Kulasegaram, G. Nikolakopoulos, E. Hatzis, R. M. Moss, J. P. Parisot, H. Yang, P. E. Czabotar, W. D. Fairlie, E. F. Lee, J. M. Adams, L. Chen, M. F. van Delft, K. N. Lowes, A. Wei, D. C. S. Huang, P. M. Colman, I. P. Street, J. B. Baell, K. Watson, and G. Lessene, J. Med. Chem., 56, 5514 (2013).
G. Inzelt, Conducting Polymers: A New Era in Electrochemistry, Springer, New York (2012), p. 23.
D. M. Knapp, E. P. Gillis, and M. D. Burke, J. Am. Chem. Soc., 131, 6961 (2009).
Y. Yamamoto, M. Takizawa, X.-Q. Yu, and N. Miyaura, Angew. Chem., Int. Ed., 47, 928 (2008).
G. A. Molander, B. Canturk, and L. E. Kennedy, J. Org. Chem., 74, 973 (2009).
N. A. Bumagin, N. P. Andryukhova, and I. P. Beletskaya, Izv. Akad. Nauk SSSR, Ser. Khim., 1449 (1988). [Bull. Acad. Sci. USSR, Div. Chem. Sci., 37, 1285 (1988).]
N. A. Bumagin, P. G. More, and I. P. Beletskaya, J. Organomet. Chem., 371, 397 (1989).
N. A. Bumagin, V. V. Bykov, and I. P. Beletskaya, Izv. Akad. Nauk SSSR, Ser. Khim., 2394 (1989). [Bull. Acad. Sci. USSR, Div. Chem. Sci., 38, 2206 (1989).]
N. A. Bumagin, V. V. Bykov, and I. P. Beletskaya, Izv. Akad. Nauk SSSR, Ser. Khim., 2672 (1990). [Bull. Acad. Sci. USSR, Div. Chem. Sci., 39, 2426 (1990).]
N. A. Bumagin, V. V. Bykov, and I. P. Beletskaya, Dokl. Akad. Nauk SSSR, 315, 1133 (1990).
A. I. Roshchin, N. A. Bumagin, and I. P. Beletskaya, Tetrahedron Lett., 36, 125 (1995).
N. A. Bumagin and V. V. Bykov, Tetrahedron, 53, 14437 (1997).
A. L. Casalnuovo and J. C. Calabrese, J. Am. Chem. Soc., 112, 4324 (1990).
M. Safi and D. Sinou, Tetrahedron Lett., 32, 2025 (1991).
J.-P. Genet, E. Blart, and M. Savignac, Synlett, 715 (1992).
T. Jeffery, Tetrahedron Lett., 35, 3051 (1994).
N. A. Bumagin, V. V. Bykov, L. I. Sukhomlinova, T. P. Tolstaya, and I. P. Beletskaya, J. Organomet. Chem., 486, 259 (1995).
N. A. Bumagin, L. I. Sukhomlinova, E. V. Luzikova, T. P. Tolstaya, and I. P. Beletskaya, Tetrahedron Lett., 37, 897 (1996).
D. Badone, M. Baroni, R. Cardamone, A. Ielmini, and U. Guzzi, J. Org. Chem., 62, 7170 (1997).
V. Polshettiwar, A. Decottignies, C. Len, and A. Fihri, ChemSusChem, 3, 502 (2010).
M. Lamblin, L. Nassar-Hardy, J.-C. Hierso, E. Fouquet, and F.-X. Felpin, Adv. Synth. Catal., 352, 33 (2010).
M. Bakherad, Appl. Organomet. Chem., 27, 125 (2013).
N. E. Leadbeater, Chem. Commun., 2881 (2005).
N. E. Leadbeater and M. Marco, Org. Lett., 4, 2973 (2002).
R. K. Arvela, N. E. Leadbeater, M. S. Sangi, V. A. Williams, P. Granados, and R. D. Singer, J. Org. Chem., 70, 161 (2005).
N. A. Isley, F. Gallou, and B. H. Lipshutz, J. Am. Chem. Soc., 135, 17707 (2013).
V. I. Potkin, N. A. Bumagin, S. K. Petkevich, A. S. Lyakhov, D. A. Rudakov, M. V. Livantsov, and N. E. Golantsov, Synthesis, 44, 151 (2012).
N. A. Bumagin, S. K. Petkevich, A. V. Kletskov, M. V. Livantsov, N. E. Golantsov, and V. I. Potkin, Khim. Geterotsikl. Soedin., 1633 (2013). [Chem. Heterocycl. Compd., 49, 1515 (2013).]
M. L. Read, A. Krapp, P. O. Miranda, and L.-L. Gundersen, Tetrahedron, 68, 1869 (2012).
V. V. Bykov and N. A. Bumagin, Izv. Akad. Nauk, Ser. Khim., 1401 (1997). [Russ. Chem. Bull., 46, 1346 (1997).]
A. Leyva-Pérez, J. Oliver-Meseguer, and P. Rubio-Marqués, A. Corma, Angew. Chem., Int. Ed., 52, 11554 (2013).
D. N. Korolev and N. A. Bumagin, Tetrahedron Lett., 46, 5751 (2005).
M. Solbakken and J. Skramstad, Acta Chem. Scand., 47, 1214 (1993).
P. A. S. Smith and J. H. Boyer, J. Am. Chem. Soc., 73, 2626 (1951).
M. Marinozzi, A. Carotti, E. Sansone, A. Macchiarulo, E. Rosatelli, R. Sardella, B. Natalini, G. Rizzo, L. Adorini, D. Passeri, F. De Franco, M. Pruzanski, and R. Pellicciari, Bioorg. Med. Chem., 20, 3429 (2012).
M. A. Ismail, J. Chem. Res., 733 (2006).
S. L. Buchwald and J. R. Naber, Adv. Synth. Catal., 350, 957 (2008).
M. Baghbanzadeh, C. O. Kappe, and C. Pilger, J. Org. Chem., 76, 8138 (2011).
A. N. Rumyantsev, V. I. Terenin, and L. G. Yudin, Khim. Geterotsikl. Soedin., 368 (1986). [Chem. Heterocycl. Compd., 22, 300 (1986).]
S.-H. Kim and R. D. Rieke, J. Org. Chem., 78, 1984 (2013).
Y. Li, Y.-J. Ding, J.-Y. Wang, Y.-M. Su, and X.-S. Wang, Org. Lett., 15, 2574 (2013).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 24-31, 2014.
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Bumagin, N.A., Veselov, I.S. & Belov, D.S. An Effective Activation of Palladium Phosphine Complexes in Aqueous Phase Reactions of Hetero-Aromatic Boronic Acids with Aryl Halides. Chem Heterocycl Comp 50, 19–25 (2014). https://doi.org/10.1007/s10593-014-1443-1
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DOI: https://doi.org/10.1007/s10593-014-1443-1