RSC Advances
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varying the haloarene and Grignard reagent also produced the 16 R. Kou, Y. Shao, D. Wang, M. H. Engelhard, J. H. Kwak,
expected coupled product with good to excellent yields. Inter-
estingly, this catalyst was found to be equally active for the
oxidative addition to the sp C–F bond. Our results conrmed
J. Wang, V. V. Viswanathan, C. Wang, Y. Lin, Y. Wang,
I. A. Aksay and J. Liu, Electrochem. Commun., 2009, 11,
954–957.
2
that Ni/RGO-40 is a promising catalyst as a replacement of Pd- 17 P. Mondal, A. Sinha, N. Salam, A. S. Roy, N. R. Jana and
based and other ligand-stabilized homogeneous catalysts. S. M. Islam, RSC Adv., 2013, 3, 5615–5623.
Among notable features, the Ni/RGO-40 would be commercially 18 S. O. Moussa, L. S. Panchakarla, M. Q. Ho and M. S. El-Shall,
economical, can overcome the difficulty concerning the ACS Catal., 2014, 4, 535–545.
recovery from the reaction mixture and was found to be 19 Z. Ji, X. Shen, G. Zhu, H. Zhou and A. Yuan, J. Mater. Chem.,
potentially recyclable. Ni/RGO-40 has enough potential as an 2012, 22, 3471–3477.
economic high performance reusable catalyst and can be of 20 X. Chen, H. Ke and G. Zou, ACS Catal., 2014, 4, 379–385.
technological viability.
21 G. A. Molander and O. A. Argintaru, Org. Lett., 2014, 16,
904–1907.
2 R. Martin and S. L. Buchwald, J. Am. Chem. Soc., 2007, 129,
844–3845.
23 S. Lou and G. C. Fu, J. Am. Chem. Soc., 2010, 132, 1264–1266.
1
2
Conflict of interest
3
The authors declare no competing nancial interest.
2
2
2
4 K. Tamao, K. Sumitani and M. Kumada, J. Am. Chem. Soc.,
972, 94, 4374.
5 R. J. P. Corriu and J. P. Masse, J. Chem. Soc., Chem.
Commun., 1972, 144a.
1
Acknowledgements
K.B. and D.S. thank the CSIR, India for providing fellowships.
6 N. Liu and Z. X. Wang, J. Org. Chem., 2011, 76, 10031–10038.
Notes and references
27 N. Yoshikai, H. Matsuda and E. Nakamura, J. Am. Chem. Soc.,
009, 131, 9590–9599.
8 M. M. Heravi and P. Hajiabbasi, Monatsh. Chem., 2012, 143,
575–1592.
9 K. Bhowmik, A. Mukherjee, M. K. Mishra and G. De,
Langmuir, 2014, 30, 3209–3216.
2
1
B. F. Machado and P. Serp, Catal. Sci. Technol., 2012, 2, 54–
5.
2
2
3
3
3
7
1
2
3
P. V. Kamat, J. Phys. Chem. Lett., 2010, 1, 520–527.
Y. Gao, D. Ma, C. Wang, J. Guan and X. Bao, Chem. Commun.,
2011, 47, 2432–2434.
0 S. H. Wu and D. H. Chen, J. Colloid Interface Sci., 2003, 259,
4
5
S. Moussa, A. R. Siamaki, B. F. Gupton and M. S. El-Shall,
ACS Catal., 2012, 2, 145–154.
282–286.
1 J. Wang, X. Zhang, Z. Wang, L. Wang and Y. Zhang, Energy
Environ. Sci., 2012, 5, 6885–6888.
H. G ¨o ksu, S. F. Ho, O. Metin, K. Korkmaz, A. M. Garcia,
M. S. G u¨ ltekin and S. Sun, ACS Catal., 2014, 4, 1777–1782.
O. C. Compton and S. T. Nguyen, Small, 2010, 6, 711–723.
H. Bai, C. Li and G. Shi, Adv. Mater., 2011, 23, 1089–1115.
G. M. Scheuermann, L. Rumi, P. Steurer, W. Bannwarth and
R. Mulhaupt, J. Am. Chem. Soc., 2009, 131, 8262–8270.
Y. Li, X. Fan, J. Qi, J. Ji, S. Wang, G. Zhang and F. Zhang, Nano
Res., 2010, 3, 429–437.
¨
2 S. D. Jackson, J. Wills, G. J. Kelly, G. D. McLellan, G. Webb,
S. Mather, R. B. Moyes, S. Simpson, P. B. Wells and
R. Whymen, Phys. Chem. Chem. Phys., 1999, 1, 2573–2580.
3 L. Saikia, D. Dutta and D. K. Dutta, Catal. Commun., 2012, 19,
6
7
8
3
3
3
3
1
–4.
4 L. Wu, J. Ling and Z. Wu, Adv. Synth. Catal., 2011, 353, 1452–
456.
9
1
1
1
1
1
1
1
0 Z. Tang, S. Shen, J. Zhuang and X. Wang, Angew. Chem., Int.
Ed., 2010, 49, 4603–4607.
1 A. R. Siamaki, A. E. R. S. Khder, V. Abdelsayed, M. S. El-Shall
and B. F. Gupton, J. Catal., 2011, 279, 1–11.
2 Y. Li, X. B. Fan, J. J. Qi, J. Y. Ji, S. L. Wang, G. L. Zhang and
F. B. Zhang, Mater. Res. Bull., 2010, 45, 1413–1418.
3 E. Yoo, T. Okada, T. Akita, M. Kohyama, I. Honma and
J. Nakamura, J. Power Sources, 2011, 196, 110–115.
4 M. Bayati, J. M. Abad, R. J. Nichols and D. J. Schiffrin, J. Phys.
Chem. C, 2010, 114, 18439–18448.
5 S. Sharma, A. Ganguly, P. Papakonstantinou, X. Miao, M. Li,
J. L. Hutchison, M. Delichatsios and S. Ukleja, J. Phys. Chem.
C, 2010, 114, 19459–19466.
5 G. Cahiez, C. Chaboche, F. Mahuteau-Betzer and M. Ahr,
Org. Lett., 2005, 7, 1943–1946.
6 A. C. Ferrari, J. C. Meyer, V. Scardaci, C. Casiraghi,
M. Lazzeri, F. Mauri, S. Piscane, D. Jiang, K. S. Novoselov,
S. Roth and A. K. Geim, Phys. Rev. Lett., 2006, 97, 187401.
7 C. Fu, G. Zhao, H. Zhang and S. Li, Int. J. Electrochem. Sci.,
3
3
2014, 9, 46–60.
8 S. Pisana, M. Lazzeric, C. Casiraghi, K. S. Novoselov,
A. K. Geim, A. C. Ferrari and F. Mauri, Nat. Mater., 2007, 6,
1
98–201.
9 W. Chan, S. Li, C. Chen and L. Yan, Adv. Mater., 2011, 23,
679–5683.
3
5
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