DOI: 10.1039/C6CC00143B
ChemComm
2
012, 11, 690; (b) H. M. Torres Galvis, J. H. Bitter, C. B. Khare, M.
about the synergistic effect between Pd and Cu
hydrogenation of alkynes was reported. There may be a new
reaction mechanism of this Pd-Cu O catalyst, which needs further
investigation and will show in the future work.
In summary, we produced Pd-Cu O nanocomposite catalyst,
which was a lead-free catalyst with better performance than
conventional Lindlar catalyst. The catalyst showed unprecedented
double selectivity in semi-hydrogenation of alkynes: only
terminal alkynes were hydrogenated, and only corresponding
2
O in selective
Ruitenbeek, A. I. Dugulan, K. P. de Jong, Science, 2012, 335, 835.
(a) F. Studt, F. Abild-Pedersen, T. Bligaard, R. Z. Sorensen, C. H.
Christensen, J. K. Norskov, Science, 2008, 320, 1320; (b) S. Carenco,
A. Leyva-Pérez, P. Concepción, C. Boissière, N. Mézailles, C.
Sanchez, A. Corma, Nano Today, 2012, 7, 21; (c) Y. Chen, C. Li, J.
Zhou, S. Zhang, D. Rao, S. He, M. Wei, D. G. Evans, X. Duan, ACS
Catal., 2015, 5, 5756.
7
2
2
8
M. Yan, T. Jin, Y. Ishikawa, T. Minato, T. Fujita, L.-Y. Chen, M.
Bao, N. Asao, M.-W. Chen, Y. Yamamoto, J. Am. Chem. Soc., 2012,
1
34, 17536.
K. H. Lee, B. Lee, K. R. Lee, M. H. Yi, N. H. Hur, Chem. Commun.,
012, 48, 4414.
A. Papp, Á. Molnár, Á. Mastalir, Appl. Catal. A: Gen, 2005, 289, 256.
9
1
2
alkenes were produced. Cu O played a vital role in suppressing
over hydrogenation of terminal alkynes to alkanes as well as
hydrogenation of internal alkynes. The synergistic effect between
2
0
11 (a) X. Song, L. Xu, Z. Yin, Y. Sun, J. Mater. Chem. A, 2013, 1,
1
2
2361; (b) L.-I. Hung, C.-K. Tsung, W. Huang, P. Yang, Adv. Mater.,
010, 22, 1910. c) Z. Sun, J. Masa, W. Xia, D. König, A. Ludwig, Z.-
2
Pd and Cu O makes this catalyst can be used in wide range of
selective semi-hydrogenation of alkynes.
A. Li, M. Farle, W. Schuhmann, M. Muhler, ACS Catal., 2012, 2,
647.
12 H. Liu, T. Jiang, B. Han, S. Liang, Y. Zhou, Science, 2009, 326, 1250.
1
The authors thank the financial supports from the National
Natural Science Foundation of China (NSFC 21573244,
1
3
(a) H. Yang, T. Zhou, W. Zhang, Angew. Chem. Int. Ed., 2013, 52,
455; (b) E. M. Zahran, N. M. Bedford, M. A. Nguyen, Y.-J. Chang,
7
2
1333009, 21573245) and the Chinese Academy of Sciences
B. S. Guiton, R. R. Naik, L. G. Bachas, M. R. Knecht, J. Am. Chem.
Soc., 2014, 136, 32.
(KJCX2-YW-N41).
1
4
(a) X. Huang, Y. Li, Y. Chen, E. Zhou, Y. Xu, H. Zhou, X. Duan, Y.
Huang, Angew. Chem. Int. Ed., 2013, 52, 2520; (b) H. Qi, P. Yu, Y.
Wang, G. Han, H. Liu, Y. Yi, Y. Li, L. Mao, J. Am. Chem. Soc., 2015,
137, 5260; (c) Y. M. A. Yamada, Y. Yuyama, T. Sato, S. Fujikawa,
Y. Uozumi, Angew. Chem. Int. Ed., 2014, 53, 127.
Notes and references
a
Beijing National Laboratory for Molecular Sciences, Laboratory of
Molecular Nanostructures and Nanotechnology, Institute of Chemistry,
Chinese Academy of Sciences, 100190, Beijing, China.
École Polytechnique Fédérale de Lausanne (EPFL), Institute of
15 a) X. Zhao, Y. Zhao, G. Fu, N. Zheng, Chem. Commun., 2015, 51,
12016; b) L. Peng, J. Zhang, J. Li, B. Han, Z. Xue, G. Yang, Angew.
Chem. Int. Ed., 2013, 52, 1792; c) S. Yang, C. Cao, L. Peng, P.
Huang, Y. Sun, F. Wei, W. Song, Chem. Commun., 2016, 52, 1575; d)
S. Yang, C. Cao, Y. Sun, P. Huang, F. Wei, W. Song, Angew. Chem.
Int. Ed., 2015, 54, 2661.
b
Chemical Sciences and Engineering, EPFL-ISIC-Valais, Sion,
Switzerland.
c
Beijing National Laboratory for Molecular Sciences, Laboratory of
Colloid and Interface and Thermodynamics, Institute of Chemistry,
Chinese Academy of Sciences, Beijing 100190, China.
Fax: +86-10-62557908; Tel: +86-10-62557908;
1
6
D. Deng, Y. Yang, Y. Gong, Y. Li, X. Xu, Y. Wang, Green Chem.,
013, 15, 2525.
2
1
7
(a) M. D. Marcinkowski, A. D. Jewell, M. Stamatakis, M. B. Boucher,
E. A. Lewis, C. J. Murphy, G. Kyriakou, E. C. H. Sykes, Nat. Mater.,
†
Electronic Supplementary Information (ESI) available: Materials,
2
013, 12, 523; (b) G. Kyriakou, M. B. Boucher, A. D. Jewell, E. A.
experimental details, and characterization. See DOI: 10.1039/b000000x/
Lewis, T. J. Lawton, A. E. Baber, H. L. Tierney, M. Flytzani-
Stephanopoulos, E. C. H. Sykes, Science, 2012, 335, 1209.
1
(a) C. Oger, L. Balas, T. Durand, J.-M. Galano, Chem. Rev., 2013,
13, 1313; (b) R. Chinchilla, C. Nájera, Chem. Rev., 2014, 114, 1783;
c) M. Crespo-Quesada, F. Cárdenas-Lizana, A.-L. Dessimoz, L.
1
(
Kiwi-Minsker, ACS Catal., 2012, 2, 1773.
2
3
(a) H. Lindlar, Helv. Chim. Acta., 1952, 35, 446; (b) Org. Synth.,
1
966, 46, 89.
(a) L. Peng, J. Zhang, S. Yang, B. Han, X. Sang, C. Liu, G. Yang,
Green Chem., 2015, 17, 4178; (b) L. Peng, J. Zhang, S. Yang, B. Han,
X. Sang, C. Liu, G. Yang, Chem. Commun., 2014, 50, 11957; (c) Y.
Yabe, T. Yamada, S. Nagata, Y. Sawama, Y. Monguchi, H. Sajiki,
Adv. Synth. Catal., 2012, 354, 1264; (d) T. Mitsudome, Y. Takahashi,
S. Ichikawa, T. Mizugaki, K. Jitsukawa, K. Kaneda, Angew. Chem.
Int. Ed., 2013, 52, 1481; (e) W. Long, N. A. Brunelli, S. A. Didas, E.
W. Ping, C. W. Jones, ACS Catal., 2013, 3, 1700; (f) W. Niu, Y. Gao,
W. Zhang, N. Yan, X. Lu, Angew. Chem. Int. Ed., 2015, 54, 8271; (g)
G. Vilé, D. Albani, M. Nachtegaal, Z. Chen, D. Dontsova, M.
Antonietti, N. López, J. Pérez-Ramírez, Angew. Chem. Int. Ed., 2015,
5
4, 11265; (h) J. Yang, F. Zhang, H. Lu, X. Hong, H. Jiang, Y. Wu,
Y. Li, Angew. Chem. Int. Ed., 2015, 54, 10889; (i) M. Armbrüster, K.
Kovnir, M. Behrens, D. Teschner, Y. Grin, R. Schlögl, J. Am. Chem.
Soc., 2010, 132, 14745; (j) N. López, C. Vargas-Fuentes, Chem.
Commun., 2012, 48, 1379.
4
(a) T. Mitsudome, M. Yamamoto, Z. Maeno, T. Mizugaki, K.
Jitsukawa, K. Kaneda, J. Am. Chem. Soc., 2015, 137, 13452; (b) M.
Stratakis, E. Vasilikogiannaki, I. Titilas, G. Vassilikogiannakis,
Chem. Commun., 2015, 51, 2384.
5
6
M. Niu, Y. Wang, W. Li, J. Jiang, Z. Jin, Catal. Commun., 2013, 38,
7
7.
(a) M. Armbrüster, K. Kovnir, M. Friedrich, D. Teschner, G.
Wowsnick, M. Hahne, P. Gille, L. Szentmiklósi, M. Feuerbacher, M.
Heggen, F. Girgsdies, D. Rosenthal, R. Schlögl, Y. Grin, Nat. Mater.,
4
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