References
1
2
3
4
K. Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett., 1975,
6, 4467.
1
K. Sonogashira, in Comprehensive Organic Synthesis, ed. B. M. Trost
and I. Fleming, Oxford, Pergamon, 1991, vol. 3, pp. 521–549.
K. Sonogashira, in Metal-Catalyzed Cross-Coupling Reactions, ed. F.
Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, pp. 203–229.
K. Sonogashira, in Handbook of Organopalladium Chemistry for
Organic Synthesis, ed. E. Negishi and A. de Meijere, Wiley-
Interscience, New York, 2002, pp. 493–529.
5
6
7
8
9
K. Sonogashira, J. Organomet. Chem., 2002, 653, 46.
R. Chinchilla and C. N ꢀa jera, Chem. Rev., 2007, 107, 874.
B. Bhanage and M. Arai, Catal. Rev. Sci. Eng., 2001, 43, 315.
J. G. de Vries, Can. J. Chem., 2001, 79, 1086.
C. E. Tucker and J. G. de Vries, Top. Catal., 2002, 19, 111.
1
1
0 C. E. Garrett and K. Prasad, Adv. Synth. Catal., 2004, 346, 889.
1 C. J. Welch, J. Albaneze-Walker, W. R. Leonard, M. Biba,
J. DaSilva, D. Henderson, B. Laing, D. J. Mathre, S. Spencer,
X. Bu and T. Wang, Org. Process Res. Dev., 2005, 9, 198.
Fig. 8 Recycling test of the Pd–Co–1(H). Reaction conditions are given
1
1
2 L. Yin and J. Liebscher, Chem. Rev., 2007, 107, 133.
3 M. A. De La Rosa, E. Velarde and A. Guzm ꢀa n, Synth. Commun.,
in Table 1.
1
990, 20, 2059.
1
1
1
1
4 K. T. Potts, C. P. Horwitz, A. Fessak, M. Keshavarz-K, K. E. Nash
and P. J. Toscano, J. Am. Chem. Soc., 1993, 115, 10444.
5 M. P. L oꢀ pez-Deber, L. Castedo and J. R. Granja, Org. Lett., 2001, 3,
2823.
6 B. M. Choudary, S. Madhi, N. S. Chowdari, M. L. Kantam and
B. Sreedhar, J. Am. Chem. Soc., 2002, 124, 14127.
7 A. H. M. de Vries, J. M. C. A. Mulders, J. H. M. Mommers,
H. J. W. Henderickx and J. G. de Vries, Org. Lett., 2003, 5, 3285.
18 S. U. Son, Y. Jang, J. Park, H. B. Na, H. M. Park, H. J. Yun, J. Lee
Pd–Co–1(H) could be easily separated from the reaction
solution via centrifugation and could be used repetitively. As
shown in Fig. 8, no significant decrease in either conversion or
selectivity was observed after being used seven times. This means
the nature of Pd active sites did not change after being used
repetitively. The catalyst weight decreased slightly after seven
consecutive runs but no significant change in the composition of
Pd–Co–1(H) was determined by ICP analysis. We thus consider
that loss of catalyst during the separation process, rather than the
leaching of Pd species from Pd–Co–1(H), was the main factor
responsible for the slight decrease of the iodobenzene conversion
during the recycling tests.
and T. Hyeon, J. Am. Chem. Soc., 2004, 126, 5026.
1
9 C. S. Consorti, F. R. Flores and J. Dupont, J. Am. Chem. Soc., 2005,
27, 12054.
20 M. B. Thathagar, P.
1
J
Kooyman, R. Boerleider, E. Jansen,
C. J. Elsevier and G. Rothenberg, Adv. Synth. Catal., 2005, 347, 1965.
1 M. B. Thathagar, J. E. ten Elshof and G. Rothenberg, Angew. Chem.,
Int. Ed., 2006, 45, 2886.
2 R. Schl o€ gl and S. B. Abd Hamid, Angew. Chem., Int. Ed., 2004, 43,
628.
3 H. Zhang, Q. Zhu, Y. Zhang, Y. Wang, L. Zhao and B. Yu, Adv.
Funct. Mater., 2007, 17, 2766.
4 S. W. Kim, M. Kim, W. Y. Lee and T. Hyeon, J. Am. Chem. Soc.,
2
2
2
2
1
Conclusions
In summary, the present work reports composition controllable
and easily reusable Pd–Co catalysts with hollow chamber
structure prepared through a vesicle-assisted chemical reduction
method. The as-prepared hollow Pd–Co catalyst exhibited much
higher activity during Sonogashira-type reactions in aqueous
medium relative to the solid Pd–Co nanoparticles by increasing
the number of Pd active sites. Other hollow bimetallic catalysts
could also be prepared based on the present method, offering
more opportunities for designing new and powerful catalysts.
2002, 124, 7642.
25 X. Chen, W. Yang, S. Wang, M. Qiao, S. Yan, K. Fan and H. He,
New J. Chem., 2005, 29, 266.
2
6 Y. Li, P. Zhou, Z. Dai, Z. Hu, P. Sun and J. Bao, New J. Chem., 2006,
0, 832.
7 F. Cheng, H. Ma, Y. Li and J. Chen, Inorg. Chem., 2007, 46, 788.
3
2
28 P. Zhou, Y. Li, P. Sun, J. Zhou and J. Bao, Chem. Commun., 2007,
418.
1
2
3
3
9 H. Li, J. Liu, S. H. Xie, M. H. Qiao, W. L. Dai, Y. F. Lu and H. X. Li,
Adv. Funct. Mater., 2008, 18, 3235.
0 H. Li, Y. Xu, J. Liu, Q. F. Zhao and H. X. Li, J. Colloid Interface Sci.,
2
009, 334, 176.
1 C. M. De Correa and F. C. Castrill oꢀ n, J. Mol. Catal. A: Chem., 2005,
28, 267.
32 P. Weightman and P. T. Andrews, J. Phys. C: Solid State Phys., 1980,
3, L815.
33 N. S. McIntyre and M. G. Cook, Anal. Chem., 1975, 47, 2208.
2
Acknowledgements
1
This work was supported by the National Natural Science
Foundation of China (20973113, 20703011), the 863 Project
34 Y. Chen, Catal. Today, 1998, 44, 3.
35 M. Ganesan, R. G. Freemantle and S. O. Obare, Chem. Mater., 2007,
(
2007AA03Z339), the 973 Program (2009CB226106), and
1
9, 3464.
Shanghai Government (09JC1411400, 09YZ158, S30406,
3
6 H. Li, J. Liu, S. H. Xie, M. H. Qiao, W. L. Dai and H. X. Li, J. Catal.,
2008, 259, 104.
0
852nm01000).
4
370 | J. Mater. Chem., 2010, 20, 4366–4370
This journal is ª The Royal Society of Chemistry 2010