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Copyright (c) 2014 Y. Liu, X.W. Ma, P. Liu*, J.W. Xie, B. Dai
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Synthesis of 4-Vinylbiphenyl Derivatives by Pd(II)-1,2-Diamino-cyclohexane Complex Catalyzed Suzuki-Miyaura Reaction
Corresponding Author(s) : Y. Liu
Asian Journal of Chemistry,
Vol. 26 No. 23 (2014)
Abstract
A series of 4-vinylbiphenyl derivatives were synthesized by Pd(II)-1,2-diaminocyclohexane complex catalyzed Suzuki-Miyaura reactions in the presence of K3PO4·3H2O as base in toluene at 80 °C and the corresponding products achieved 39-95 % yields. According to this efficient C-C bond-forming method, the obtained yields of 4-vinylbiphenyl liquid crystal compounds were up to 89 %.
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- J.H. Kwon, S.I. Shin, J. Choi, M.H. Chung, T.Y. Oh, K.H. Kim, D.H. Choi and B.K. Ju, J. Nanosci. Nanotechnol., 10, 3198 (2010).
- N.R. Vautravers, P. Andre, A.M.Z. Slawin and D.J. Cole-Hamilton, Org. Biomol. Chem., 7, 717 (2009).
- H. Tachikawa and H. Kawabata, J. Phys. Chem. B, 107, 1113 (2003).
- J.C. Bevington and G. Ayrey, Eur. Polym. J., 23, 497 (1987).
- A. Padwa, H. Ku and A. Mazzu, J. Org. Chem., 43, 381 (1978).
- N. Miyaura and A. Suzuki, Chem. Rev., 95, 2457 (1995).
- S. Kotha, K. Lahiri and D. Kashinath, Tetrahedron, 58, 9633 (2002).
- H.A. Zayas, M.C. Bowyer, C.P. Gordon, C.I. Holdsworth and A. McCluskey, Tetrahedron Lett., 50, 5894 (2009).
- P. Liu, L. Zhou, X.G. Li and R. He, J. Organomet. Chem., 694, 2290 (2009).
- P. Liu, W.Z. Zhang and R. He, Appl. Organomet. Chem., 23, 135 (2009).
- P. Liu, X.J. Feng and R. He, Tetrahedron, 66, 631 (2010).
- P. Liu, M. Yan and R. He, Appl. Organomet. Chem., 24, 131 (2010).
- Y. Liu, X.W. Ma, J.W. Xie, P. Liu, B. Dai and R. He, Appl. Organomet. Chem., 27, 494 (2013).
- X.W. Ma, Y. Liu, P. Liu, J.W. Xie, B. Dai and Z.Y. Liu, Appl. Organomet. Chem., 27, 707 (2013).
- J.M. Tercero-Moreno, A. Matilla-Hernández, S. González-García and J. Niclós-Gutiérrez, Inorg. Chim. Acta, 253, 23 (1996).
- J.-Y. Kim, Arch. Pharm. Res., 15, 336 (1992).
References
J.H. Kwon, S.I. Shin, J. Choi, M.H. Chung, T.Y. Oh, K.H. Kim, D.H. Choi and B.K. Ju, J. Nanosci. Nanotechnol., 10, 3198 (2010).
N.R. Vautravers, P. Andre, A.M.Z. Slawin and D.J. Cole-Hamilton, Org. Biomol. Chem., 7, 717 (2009).
H. Tachikawa and H. Kawabata, J. Phys. Chem. B, 107, 1113 (2003).
J.C. Bevington and G. Ayrey, Eur. Polym. J., 23, 497 (1987).
A. Padwa, H. Ku and A. Mazzu, J. Org. Chem., 43, 381 (1978).
N. Miyaura and A. Suzuki, Chem. Rev., 95, 2457 (1995).
S. Kotha, K. Lahiri and D. Kashinath, Tetrahedron, 58, 9633 (2002).
H.A. Zayas, M.C. Bowyer, C.P. Gordon, C.I. Holdsworth and A. McCluskey, Tetrahedron Lett., 50, 5894 (2009).
P. Liu, L. Zhou, X.G. Li and R. He, J. Organomet. Chem., 694, 2290 (2009).
P. Liu, W.Z. Zhang and R. He, Appl. Organomet. Chem., 23, 135 (2009).
P. Liu, X.J. Feng and R. He, Tetrahedron, 66, 631 (2010).
P. Liu, M. Yan and R. He, Appl. Organomet. Chem., 24, 131 (2010).
Y. Liu, X.W. Ma, J.W. Xie, P. Liu, B. Dai and R. He, Appl. Organomet. Chem., 27, 494 (2013).
X.W. Ma, Y. Liu, P. Liu, J.W. Xie, B. Dai and Z.Y. Liu, Appl. Organomet. Chem., 27, 707 (2013).
J.M. Tercero-Moreno, A. Matilla-Hernández, S. González-García and J. Niclós-Gutiérrez, Inorg. Chim. Acta, 253, 23 (1996).
J.-Y. Kim, Arch. Pharm. Res., 15, 336 (1992).