RSC Advances
Paper
the particle coalescence, resulting in a very stable colloidal 11 J. Garc ´ı a-Mart ´ı nez, R. W. J. Scott and R. M. Crooks, J. Am.
dispersion for a long time. Size and morphology of the Chem. Soc., 2003, 125, 11190–11191.
dispersed-PdNPs depend on the value of current density 12 N. Toshima, Y. Shiraishi, T. Teranishi, M. Miyake,
applied, the efficient stirring of the solution and the appropriate
T. Tominaga, H. Watanabe, W. Brijoux, H. B ¨o nnemann
concentration of the stabilizing agent. The increase of PVP
and G. Schmid, Appl. Organomet. Chem., 2001, 15, 178–196.
concentration did not produce noticeable changes on the 13 D. Bera, S. C. Kuiry and S. Seal, J. Phys. Chem. B, 2004, 108,
average dimensions and the potential-time transient. In addi- 556–562.
tion, TEM images analysis evidences the presence of a ne 14 F. Li, B. Zhang, S. Dong and E. Wang, Electrochim. Acta, 1997,
structure (tiny particles) decorating the Pd backbone when they
42, 2563–2568.
ꢀ2
are obtained at current densities higher than ꢀ250 mA cm
,
15 G. Corthey, A. A. Rubert, A. L. Picone, G. Casillas,
L. J. Giovanetti, J. M. Ramallo-L ´o pez, E. Zelaya,
G. A. Benitez, F. G. Requejo, M. J. Yacam ´a n,
R. C. Salvarezza and M. H. Fonticelli, J. Phys. Chem. C,
2012, 116, 9830–9837.
which may be consequence of the simultaneous occurrence of
hydrogen evolution reaction on the electrode surface.
Although precise control of the uniform size of the nano-
particles can not be reached with electrochemical synthesis
methods, the obtained PVP–PdNPs dispersions have a very high 16 T. R. Soreta, J. Strutwolf, O. Henry and C. K. O'Sullivan,
catalytic activity in Suzuki and Heck coupling reactions in Langmuir, 2010, 26, 12293–12299.
aqueous media. This catalyst allowed performing the coupling 17 X.-L. Tang, P. Jiang, G.-L. Ge, M. Tsuji, S.-S. Xie and Y.-J. Guo,
reaction in aqueous medium, under no harsh conditions, in Langmuir, 2008, 24, 1763–1768.
short reaction time, with very low catalyst loading and with very 18 A. B. Patil, S. R. Lanke, K. M. Deshmukh, A. B. Pandit and
good yields and selectivity for the coupling products. Even B. M. Bhanage, Mater. Lett., 2012, 79, 1–3.
deactivated aryl bromides can be used, and outstanding very 19 B. Yin, H. Ma, S. Wang and S. Chen, J. Phys. Chem. B, 2003,
high TOFs values were obtained. It is important to point out 107, 8898–8904.
that the PVP–PdNPs catalyst were employ as-prepared, without 20 M. T. Reetz, R. Breinbauer and K. Wanninger, Tetrahedron
further purication, and they can be stored for several months Lett., 1996, 37, 4499–4502.
since no precipitation was observed. Finally, this catalytic 21 P. M. Uberman, L. A. P ´e rez, G. I. Lacconi and S. E. Mart ´ı n,
system could be reused and proved to be an environmental
friendly alternative to conventional Pd catalyst.
J. Mol. Catal. A: Chem., 2012, 363–364, 245–253.
22 C. Deraedt and D. Astruc, Acc. Chem. Res., 2014, 47, 494–503.
23 C. Deraedt, L. Salmon, L. Etienne, J. Ruiz and D. Astruc,
Chem. Commun., 2013, 49, 8169–8171.
Acknowledgements
2
4 K. M. Deshmukh, Z. S. Qureshi, K. D. Bhatte,
K. A. Venkatesan, T. G. Srinivasan, P. R. V. Raob and
B. M. Bhanage, New J. Chem., 2011, 35, 2747–2751.
5 J. Liu, F. He, T. M. Gunn, D. Zhao and C. B. Roberts,
Langmuir, 2009, 25, 7116–7128.
The research was supported by CONICET, FONCyT and SECyT-
UNC. L.A.P. and P.M.U. are very grateful to CONICET for the
fellowships.
2
2
2
6 M. Studer, H.-U. Blaser and C. Exner, Adv. Synth. Catal., 2003,
345, 45–65.
References
7 B. F. G. Johnson, Top. Catal., 2003, 24, 147–159.
1
U. Heiz and U. Landman, in Nanocatalysis, Springer, Berlin, 28 A. Balanta, C. Godard and C. Claver, Chem. Soc. Rev., 2011,
007. 40, 4973–4985.
D. Peral, F. G ´o mez-Villarraga, X. Sala, J. Pons, J. C. Bay ´o n, 29 N. T. S. Phan, M. van der Sluys and C. W. Jones, Adv. Synth.
2
2
J. Ros, M. Guerrero, L. Vendier, P. Lecante, J. Garc ´ı a-Ant ´o n
and K. Philippot, Catal. Sci. Technol., 2013, 3, 475–589.
Catal., 2006, 348, 609–679.
30 A. Suzuki, Angew. Chem., Int. Ed., 2011, 50, 6722–6737.
31 V. Polshettiwar, A. Decottignies, C. Len and A. Fihri,
ChemSusChem, 2010, 3, 502–522.
´
´
3
4
5
A. Molnar, Chem. Rev., 2011, 111, 2251–2320.
D. Astruc, Inorg. Chem., 2007, 46, 1884–1894.
Y. Gimeno, A. Hern ´a ndez Creus, P. Carro, S. Gonz ´a lez, 32 J. Hassan, M. Sevignon, C. Gozzi, E. Schulz and M. Lemaire,
R. C. Salvarezza and A. J. Arvia, J. Phys. Chem. B, 2002, 106,
232–4244.
F. Li, B. Zhang, S. Dong and E. Wang, Electrochim. Acta, 1997,
2, 2563–2568.
M. T. Reetz and W. Helbig, J. Am. Chem. Soc., 1994, 116,
401–7402.
D. Bera, S. C. Kuiry and S. Seal, J. Phys. Chem. B, 2004, 108,
56–562.
Chem. Rev., 2002, 102, 1359–1470.
33 A. N. Cammidge and K. V. L. Cr ´e py, Tetrahedron, 2004, 60,
4377–4386.
34 T. E. Barder, S. D. Walker, J. R. Martinelli and S. L. Buchwald,
J. Am. Chem. Soc., 2005, 127, 4685–4696.
35 K. Sambasivarao and M. Kalyaneswar, Chem.–Asian J., 2009,
4, 354–362.
4
6
7
8
9
4
7
5
36 N. Miyaura, Top. Curr. Chem., 2002, 219, 11–59.
W. Pan, X. Zhang, H. Ma and J. Zhang, J. Phys. Chem. C, 2008, 37 R. Martin and S. L. Buchwald, Acc. Chem. Res., 2008, 41,
12, 2456–2461. 1461–1473.
0 S. S. Shendage, U. B. Patil and J. M. Nagarkar, Tetrahedron 38 F. Alonso, I. P. Beletskaya and M. Yus, Tetrahedron, 2005, 61,
Lett., 2013, 54, 3457–3461. 11771–11835.
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1
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