An Efficient and Recyclable Catalytic System: PdCl2-Dppc+ -PF6– -[bmim][PF6] for Heck Coupling Reaction

Liang Liu; Xiao Ming Song; Jin Tao Guan; Zhi Yong Zhang; Ben Mei Wei

doi:10.14233/ajchem.2015.17749

Issue

Vol. 27 No. 6 (2015): Vol 27 Issue 6

Issue Published : March 17, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

An Efficient and Recyclable Catalytic System: PdCl2-Dppc+ -PF6– -[bmim][PF6] for Heck Coupling Reaction

https://doi.org/10.14233/ajchem.2015.17749

Liang Liu

School of Biology and Pharmaceutical Engineering, Wuhan Polytechnic University, Wuhan, P.R. China

Xiao Ming Song

School of Chemical and Environmental Engineering, Wuhan Polytechnic University, Wuhan, P.R. China

Jin Tao Guan

School of Chemical and Environmental Engineering, Wuhan Polytechnic University, Wuhan, P.R. China

Zhi Yong Zhang

School of Chemical and Environmental Engineering, Wuhan Polytechnic University, Wuhan, P.R. China

Ben Mei Wei

School of Chemical and Environmental Engineering, Wuhan Polytechnic University, Wuhan, P.R. China

Corresponding Author(s) : Jin Tao Guan

guanjintao@126.com

Asian Journal of Chemistry, Vol. 27 No. 6 (2015): Vol 27 Issue 6
Article Published : March 18, 2015

Abstract

An efficient PdCl₂-Dppc⁺-PF₆^–-[bmim][PF₆] catalytic system has been developed for the Heck coupling reaction of various aryl iodides with olefins. The catalytic system allows the coupling reaction to proceed smoothly in excellent yields and can be recycled 5 times with minimal loss of activity.

Keywords

Dppc -PF6– Heck coupling reaction Recyclable

Liu, L., Ming Song, X., Tao Guan, J., Yong Zhang, Z., & Mei Wei, B. (2015). An Efficient and Recyclable Catalytic System: PdCl2-Dppc+ -PF6– -[bmim][PF6] for Heck Coupling Reaction. Asian Journal of Chemistry, 27(6), 2093–2095. https://doi.org/10.14233/ajchem.2015.17749

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References

M. Oestrich, The Mizoroki-Heck Reaction, Wiley, Chichester, edn. 4 (2009).
R.F. Heck, in eds.: B.M. Trost and I. Fleming, Comprehensive Organic Synthesis, Pergamon Press, Oxford, Vol. 4, pp. 833-863 (1991).
I.P. Beletskaya and A.V. Cheprakov, Chem. Rev., 100, 3009 (2000); doi:10.1021/cr9903048.
E.A.B. Kantchev, C.J. O'Brien and M.G. Organ, Angew. Chem. Int. Ed., 46, 2768 (2007); doi:10.1002/anie.200601663.
R. Ferraccioli, Synthesis, 45, 581 (2013); doi:10.1055/s-0032-1318218.
P.T. Anastas, L.B. Bartlett, M.M. Kirchhoff and T.C. Williamson, Catal. Today, 55, 11 (2000); doi:10.1016/S0920-5861(99)00222-9.
P.T. Anastas and R.L. Lankey, Green Chem., 2, 289 (2000); doi:10.1039/b005650m.
R.L. Lankey and P.T. Anastas, ACS Symposium Series 823, American Chemical Society: Washington, DC, p. 26 (2002).
S.V. Jagtap and R.M. Deshpande, Asian J. Chem., 25, 8633 (2013); doi:10.14233/ajchem.2013.14874.
V. Calo, A. Nacci, A. Monopoli, A. Fornaro, L. Sabbatini, N. Cioffi and N. Ditaranto, Organometallics, 23, 5154 (2004); doi:10.1021/om049586e.
Z. Wu, Q. Wu, M. Chen and T. Tao, Asian J. Chem., 25, 5783 (2013); doi:10.14233/ajchem.2013.OH90.
L.R. Moore and K.H. Shaughnessy, Org. Lett., 6, 225 (2004); doi:10.1021/ol0360288.
N. Nowrouzi, D. Tarokh and S. Motevalli, J. Mol. Catal. Chem., 385, 13 (2014); doi:10.1016/j.molcata.2014.01.005.
C.I.M. Santos, J.F.B. Barata, M.A.F. Faustino, C. Lodeiro and M.G.P.M.S. Neves, RSC Adv., 3, 19219 (2013); doi:10.1039/c3ra43493a.
Y. Wang, J. Luo and Z. Liu, J. Organomet. Chem., 739, 1 (2013); doi:10.1016/j.jorganchem.2013.04.006.
C. Premi and N. Jain, Eur. J. Org. Chem., 5493 (2013); doi:10.1002/ejoc.201300307.
J.T. Guan, G.-A. Yu, L. Chen, T. Qing Weng, J.J. Yuan and S.H. Liu, Appl. Organomet. Chem., 23, 75 (2009); doi:10.1002/aoc.1474.
J.T. Guan, T.Q. Weng, G.-A. Yu and S.H. Liu, Tetrahedron Lett., 48, 7129 (2007); doi:10.1016/j.tetlet.2007.07.207.
J.T. Guan, G. Yu, J.G. Hou, N. Yu, Y. Ren and S.H. Liu, Appl. Organomet. Chem., 21, 355 (2007); doi:10.1002/aoc.1215.
G. Yu, Y. Ren, J.T. Guan, Y. Lin and S.H. Liu, J. Organomet. Chem., 692, 3914 (2007); doi:10.1016/j.jorganchem.2007.05.046.
C.C. Brasse, U. Englert, A. Salzer, H. Waffenschmidt and P. Wasserscheid, Organometallics, 19, 3818 (2000); doi:10.1021/om000183y.
D.P. Richardson, T.E. Smith and S. Wolff, Org. Synth., 79, 236 (2002); doi:10.15227/orgsyn.079.0236.

References

M. Oestrich, The Mizoroki-Heck Reaction, Wiley, Chichester, edn. 4 (2009).

R.F. Heck, in eds.: B.M. Trost and I. Fleming, Comprehensive Organic Synthesis, Pergamon Press, Oxford, Vol. 4, pp. 833-863 (1991).

I.P. Beletskaya and A.V. Cheprakov, Chem. Rev., 100, 3009 (2000); doi:10.1021/cr9903048.

E.A.B. Kantchev, C.J. O'Brien and M.G. Organ, Angew. Chem. Int. Ed., 46, 2768 (2007); doi:10.1002/anie.200601663.

R. Ferraccioli, Synthesis, 45, 581 (2013); doi:10.1055/s-0032-1318218.

P.T. Anastas, L.B. Bartlett, M.M. Kirchhoff and T.C. Williamson, Catal. Today, 55, 11 (2000); doi:10.1016/S0920-5861(99)00222-9.

P.T. Anastas and R.L. Lankey, Green Chem., 2, 289 (2000); doi:10.1039/b005650m.

R.L. Lankey and P.T. Anastas, ACS Symposium Series 823, American Chemical Society: Washington, DC, p. 26 (2002).

S.V. Jagtap and R.M. Deshpande, Asian J. Chem., 25, 8633 (2013); doi:10.14233/ajchem.2013.14874.

V. Calo, A. Nacci, A. Monopoli, A. Fornaro, L. Sabbatini, N. Cioffi and N. Ditaranto, Organometallics, 23, 5154 (2004); doi:10.1021/om049586e.

Z. Wu, Q. Wu, M. Chen and T. Tao, Asian J. Chem., 25, 5783 (2013); doi:10.14233/ajchem.2013.OH90.

L.R. Moore and K.H. Shaughnessy, Org. Lett., 6, 225 (2004); doi:10.1021/ol0360288.

N. Nowrouzi, D. Tarokh and S. Motevalli, J. Mol. Catal. Chem., 385, 13 (2014); doi:10.1016/j.molcata.2014.01.005.

C.I.M. Santos, J.F.B. Barata, M.A.F. Faustino, C. Lodeiro and M.G.P.M.S. Neves, RSC Adv., 3, 19219 (2013); doi:10.1039/c3ra43493a.

Y. Wang, J. Luo and Z. Liu, J. Organomet. Chem., 739, 1 (2013); doi:10.1016/j.jorganchem.2013.04.006.

C. Premi and N. Jain, Eur. J. Org. Chem., 5493 (2013); doi:10.1002/ejoc.201300307.

J.T. Guan, G.-A. Yu, L. Chen, T. Qing Weng, J.J. Yuan and S.H. Liu, Appl. Organomet. Chem., 23, 75 (2009); doi:10.1002/aoc.1474.

J.T. Guan, T.Q. Weng, G.-A. Yu and S.H. Liu, Tetrahedron Lett., 48, 7129 (2007); doi:10.1016/j.tetlet.2007.07.207.

J.T. Guan, G. Yu, J.G. Hou, N. Yu, Y. Ren and S.H. Liu, Appl. Organomet. Chem., 21, 355 (2007); doi:10.1002/aoc.1215.

G. Yu, Y. Ren, J.T. Guan, Y. Lin and S.H. Liu, J. Organomet. Chem., 692, 3914 (2007); doi:10.1016/j.jorganchem.2007.05.046.

C.C. Brasse, U. Englert, A. Salzer, H. Waffenschmidt and P. Wasserscheid, Organometallics, 19, 3818 (2000); doi:10.1021/om000183y.

D.P. Richardson, T.E. Smith and S. Wolff, Org. Synth., 79, 236 (2002); doi:10.15227/orgsyn.079.0236.

Issue

Vol. 27 No. 6 (2015): Vol 27 Issue 6

An Efficient and Recyclable Catalytic System: PdCl2-Dppc+ -PF6– -[bmim][PF6] for Heck Coupling Reaction

Corresponding Author(s) : Jin Tao Guan

Abstract

Keywords

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