12 of 13
LAMEI ET AL.
[14] B. J. Gallon, R. W. Kojima, R. B. Kaner, P. L. Diaconescu, Angew.
Chem. Int. Ed. 2007, 46, 7251.
that Pd is not involved in the rate‐determining step. Based on
previous reports, Pd helps lower the required reaction tem-
perature in Cu/Pd co‐catalysed Suzuki coupling.[46,47] We
can conclude that probably the Pd‐catalysed step is
oxidative addition, and it is likely that the oxidative addition
is faster than the transmetallation or the reductive elimina-
tion at copper.
[15] U. I. Tessin, X. Bantreil, O. Songis, C. S. J. Cazin, Eur. J. Inorg.
Chem. 2013, 12, 2007.
[16] S. Handa, Y. Wang, F. Gallou, B. H. Lipshutz, Science 2015, 349,
1087.
[17] R. K. Arvela, N. E. Leadbeater, M. S. Sangi, V. A. Williams, P.
Granados, R. D. Singer, J. Org. Chem. 2005, 70, 161.
[18] M. B. Thathagar, J. Beckers, G. Rothenberg, J. Am. Chem. Soc.
2002, 124, 11858.
4 | CONCLUSIONS
[19] S. Gu, J. Huang, X. Liu, H. Liu, Y. Zhou, W. Xu, Inorg. Chem.
Commun. 2012, 21, 168.
In summary, highly dispersed Cu NPs immobilized on core–
shell Fe3O4@C MNPs functionalized with arginine as a
support with 92.8 ppm of Pd as impurity were synthesized.
The FCA‐Cu MNPs were used in the promotion of Suzuki
cross‐coupling of halobenzenes including iodinated, bromi-
nated and chlorinated substrates with phenylboronic acids.
A mixture of metal hydroxides such as KOH, Ba(OH)2,
Ca(OH)2, Mg(OH)2 as bases in water as a green and non‐
toxic solvent in the presence of the FCA‐Cu NPs led to
an efficient procedure for the Suzuki reaction at room tem-
perature. The FCA‐Cu NPs were recycled and reused for at
least six successful runs.
[20] M. B. Thathagar, J. Beckers, G. Rothenberg, Adv. Synth. Catal.
2003, 345, 979.
[21] A. S. Demir, O. Reis, M. Emrullahoglu, J. Org. Chem. 2003, 68,
10130.
[22] N. Kirai, Y. Yamamoto, Eur. J. Org. Chem. 2009, 12, 1864.
[23] Y. S. Panova, A. S. Kashin, M. G. Vorobev, E. S. Degtyareva, V. P.
Ananikov, ACS Catal. 2016, 6, 3637.
[24] A. Decottignies, A. Fihri, G. Azemar, F. Djedaini‐Pilard, C. Len,
Catal. Commun. 2013, 32, 101.
[25] V. Polshettiwar, A. Decottignies, C. Len, A. Fihri, ChemSusChem
2010, 3, 502.
[26] V. Polshettiwar, C. Len, A. Fihri, Coord. Chem. Rev. 2009, 253,
ACKNOWLEDGEMENTS
2599.
The authors gratefully acknowledged for partially financial
support of this study (Grant No: 33571) by Research Council
of Ferdowsi University of Mashhad.
[27] G. Herve, G. Sartori, G. Enderlin, G. Mackenzie, C. Len, RSC Adv.
2014, 4, 18558.
[28] S. Gallagher‐Duval, G. Hervé, G. Sartori, G. Enderlin, C. Len, New
J. Chem. 2013, 37, 1989.
[29] V. Polshettiwar, R. Luque, A. Fihri, H. B. Zhu, M. Bouhrara, J. M.
REFERENCES
Basset, Chem. Rev. 2011, 111, 3036.
[1] C. J. Li, Chem. Rev. 2005, 105, 3095.
[30] Y. H. Zhu, L. P. Stubbs, F. Ho, R. Z. Liu, C. P. Ship, J. A. Maguire,
[2] M. O. Simon, C. J. Li, Chem. Soc. Rev. 2012, 41, 1415.
[3] N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun. 1981, 11, 513.
N. S. Hosmane, ChemCatChem 2010, 2, 365.
[31] S. Shylesh, V. Schünemann, W. R. Thiel, Angew. Chem. Int. Ed.
2010, 49, 3428.
[4] C. C. C. J. Seechurn, M. O. Kitching, T. J. Colacot, V. Snieckus,
Angew. Chem. Int. Ed. 2012, 51, 5062.
[32] A. Balanta, C. Godard, C. Claver, Chem. Soc. Rev. 2011, 40, 4973.
[33] M. Gholinejad, N. Jeddi, ACS Sustain. Chem. Eng. 2014, 2, 2658.
[5] H. Li, C. C. C. J. Seechurn, T. J. Colacot, ACS Catal. 2012, 2,
1147.
[34] M. Gopiraman, S. G. Babu, Z. Khatri, W. Kai, Y. A. Kim, M. Endo,
[6] F. Bellina, A. Carpita, R. Rossi, Synthesis 2004, 15, 2419.
[7] S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633.
I. S. Kim, Carbon 2013, 62, 135.
[35] D. Talukdar, G. Das, S. Thakur, N. Karak, A. J. Thakur, Catal.
Commun. 2015, 59, 238.
[8] V. F. Slagt, A. H. M. de Vries, J. G. de Vries, R. M. Kellogg, Org.
Process Res. Dev. 2009, 14, 30.
[36] D. Azarifar, F. Soleimanei, RSC Adv. 2014, 4, 12119.
[9] J. P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651.
[37] V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J. M.
Basset, Chem. Rev. 2011, 111, 3036.
[10] A. Fihri, M. Bouhrara, B. Nekoueishahraki, J.‐M. Basset, V.
Polshettiwar, Chem. Soc. Rev. 2011, 40, 5181.
[38] N. T. Bui, T. B. Dang, H. V. Le, N. T. S. Phan, Chin. J. Catal.
2011, 32, 1667.
[11] A. Molnar, Chem. Rev. 2011, 111, 2251.
[39] P. R. Boruah, A. A. Ali, M. Chetia, B. Saikia, D. Sarma, Chem.
Commun. 2015, 51, 11489.
[12] A. Grirrane, A. Corma, H. Garcia, Science 2008, 322, 1661.
[13] L. Kesavan, R. Tiruvalam, M. H. Ab Rahim, M. I. bin Saiman, D. I.
Enache, R. L. Jenkins, N. Dimitratos, J. A. Lopez‐Sanchez, S. H.
Taylor, D. W. Knight, C. J. Kiely, G. J. Hutchings, Science 2011,
331, 195.
[40] M. Hojjati‐Rad, H. Eshghi, S. M. Seyyedi, M. Rahimizadeh, F.
Eshkil, K. Lamei, J. Iran. Chem. Soc. 2016, 13, 1105.
[41] S. Rostamnia, K. Lamei, F. Pourhassan. RSC Adv. 2014, 4, 59626.