Journal of the American Chemical Society
Page 4 of 12
Ina (SPring-8) for XAFS measurements. The TEM experiments
were carried out at a facility of the Research Center for Ultrahigh
Voltage Electron Microscopy, Osaka University.
Leyva-Pérez, A.; Concepción, P.; Boissière, C.; Mézailles, N.; Sanchez, C.;
Corma, A. Nano Today 2012, 7, 21.
15) Semba, K.; Fujihara, T.; Xu, T.; Terao, J.; Tsuji, Y. Adv. Synth. Catal.
012, 354, 1542.
16) Niu, M.; Wang, Y.; Li, W.; Jiang, J.; Jin, Z. Catal. Commun. 2013,
38, 77.
1
2
3
4
5
6
7
8
9
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
2
3
3
3
3
3
3
3
3
3
3
4
4
4
4
4
4
4
4
4
4
5
5
5
5
5
5
5
5
5
5
6
(
2
(
REFERENCES
(
(
17) Lindlar, H. Helv. Chim. Acta 1952, 35, 446.
18) For gas-phase semihydrogenation of alkynes using gold catalysts, see:
(1) (a) Hagen, J. Industrial Catalysis: A Practical Approach, Wiley-VCH,
1999. (b) Ertl, G.; Knözinger, H.; Schüth, F.; Weitkamp, J. Handbook of
Heterogeneous Catalysis 2nd edn, Wiley-VCH, 2008. (c) Astruc, D. Nano-
particles and Catalysis, Wiley-VCH, 2008.
(a) Bond, G.; Sermon, P.; J. Chem. Soc., Chem. Commun. 1973, 444. (b)
Jia, J.; Haraki, K.; Kondo, J. N.; Domen, K.; Tamaru, K. J. Phys. Chem. B
2000, 104, 11153. (c) Azizi, Y.; Petit, C.; Pitchon, V. J. Catal. 2008, 256,
(2) (a) Tauster, S. J.; Fung, S. C.; Baker, R. T.; Horsley, J. A. Science
3
(
38.
19) (a) Yan, M.; Jin, T.; Ishikawa, Y.; Minato, T.; Fujita, T.; Chen, L.-Y.;
1981, 211, 1121. (b) Schubert, M. M.; Hackenberg, S.; van Veen, A. C.;
Muhler, M.; Plzak,V.; Behm, R. J. J. Catal. 2001, 197, 113. (c) Bell, A. T.
Science 2003, 299, 1688. (d) Tian, N.; Zhou, Z.-Y.; Sun, S.-G.; Ding, Y.;
Wang, Z. L. Science 2007, 316, 732. (e) Somorjai, G. A.; Park, J. Y. Angew.
Chem. Int. Ed. 2008, 47, 9212.
(3) (a) Aiken, J. D.; Finke, R. G. J. Mol. Catal. A Chem. 1999, 145, 1. (b)
Zhong, C.; Maye, M. Adv. Mater. 2001, 13, 1507. (c) Li, G.; Tang, Z. Na-
noscale 2014, 6, 3995.
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
Bao, M.; Asao, N.; Chen, M.-W.; Yamamoto, Y. J. Am. Chem. Soc. 2012,
134, 17536. (b) Shao, L.; Huang, X.; Teschner, D.; Zhang, W. ACS Catal.
2014, 4, 2369. (c) Li, S.-S.; Liu, X.; Liu, Y.-M.; He, H.-Y.; Fan, K.-N.; Cao,
Y. Chem. Commun. 2014, 50, 5626. (d) Li, G.; Jin, R. J. Am. Chem. Soc.
2
014, 136, 11347. (e) Vasilikogiannaki, E.; Titilas, I.; Vassilikogiannakis,
G.; Stratakis, M. Chem. Commun. 2015, 51, 2384. (f) Wagh, Y. S.; Asao,
N. J. Org. Chem. 2015, 80, 847.
(4) (a) Alayoglu, S.; Nilekar, A. U.; Mavrikakis, M.; Eichhorn, B. Nat.
(
20) Kluwer, A. M.; Koblenz, T. S.; Jonischkeit, T. T.; Woelk, K.; Elsevier,
C. J. J. Am. Chem. Soc. 2005, 127, 15470.
21) Polar hydrogen species preferentially react with alkynes with elec-
Mater. 2008, 7, 333. (b) Joo, S. H.; Park, J. Y.; Tsung, C.-K.; Yamada, Y.;
Yang, P.; Somorjai, G. A. Nat. Mater. 2009, 8, 126. (c) Mazumder, V.; Chi,
M.: More, K. L.; Sun, S. J. Am. Chem. Soc. 2010, 132, 7848.
(
tron-withdrawing substituents compared to alkynes without the substituents,
see: Vianello, R.; Peran, N.; Maksić, Z. B.; J. Phys. Chem. A 2006, 110,
(5) (a) Cargnello, M.; Wieder, N. L.; Montini, T.; Gorte, R. J.; Fornasiero,
P. J. Am. Chem. Soc. 2010, 132, 1402. (b) Zhou, H.-P.; Wu, H.-S.; Shen, J.;
Yin, A.-X.; Sun, L.-D.; Yan, C.-H. J. Am. Chem. Soc. 2010, 132, 4998.
(6) (a) Dravid, V. P.; Host, J. J.; Teng, M. H.; Hwang, B. E. J.; Johnson,
D. L.; Mason, T. O. J. R. Weertman Nature 1995, 374, 602. (b) Lu, J. Fu,
Kung, B. M. C.; Xiao, G.: Elam, J. W.; Kung, H. H.; Stair, P. C. Science
1
(
2870.
22) Mitsudome, T.; Noujima, A.; Mikami, Y.; Mizugaki, T.; Jitsukawa,
K.; K. Kaneda, Angew. Chem. Int. Ed. 2010, 49, 5545.
23) Noujima, A.; Mitsudome, T.; Mizugaki, T.; Jitsukawa, K.; Kaneda,
K. Angew. Chem. Int. Ed. 2011, 50, 2986.
24) For electrophilicity of alkynes, see: (a) Miller, S. I. J. Org. Chem.
956, 21, 247. (b) Dale, J. Chemistry of Acetylenes, Marcel Dekker, New
York, 1969. (c) Yu, J.; Spencer, J. B. J. Org. Chem. 1997, 62, 8618.
(
2
012, 335, 1205.
(
1
(7) (a) Yeung, C. M. Y.; Yu, K. M. K.; Fu, Q. J.; Thompsett, D.; Petch, M.
I.; Tsang, S. C. J. Am. Chem. Soc. 2005, 127, 18010. (b) Kayama, T.; Yama-
zaki, K.; Shinjoh, H. J. Am. Chem. Soc. 2010, 132, 13154. (c) Mitsudome,
T.; Mikami, Y.; Matoba, M.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. An-
gew. Chem. Int. Ed. 2012, 51, 136. (d) Mitsudome, T.; Matoba, M.; Mi-
zugaki, T.; Jitsukawa, K.; Kaneda, K. Chem. Eur. J. 2013, 19, 5255.
2
(8) For previous methods for the synthesis of Au@CeO in multi-step pro-
cesses, see: (a) Cargnello, M.; Gentilini, C.; Montini, T.; Fonda, E.;
Mehraeen, S.; Chi, M.; Herrera-Collado, M.; Browning, N. D.; Polizzi, S.;
Pasquato, L.; Fornasiero, P. Chem. Mater. 2010, 22, 4335. (b) Zhu, F.; Chen,
G.; Sun, S.; Sun, X. J. Mater. Chem. A 2013, 1, 288. (c) Wei, Y.; Zhao, Z.;
Yu, X.; Jin, B.; Liu, J.; Xu, C.; Duan, A.; Jiang, G.; Ma, S.; Catal. Sci.
Technol. 2013, 3, 2958. (d) Li, B.; Gu, T.; Ming, T.; Wang, J.; Wang, P.;
Yu, J. ACS Nano 2014, 8, 8152.
(9) There is only one report on the one-step synthesis of Au@CeO
oxidation with a mean diameter of 17 nm of Au NPs in the core and a CeO
shell with 100 nm thickness, see: Qi, J.; Chen, J.; Li, G.; Li, S.; Gao, Y.;
Tang, Z. Energy Environ. Sci. 2012, 5, 8937. However, the Au@CeO ma-
2
for CO
2
2
terial did not show any catalytic activity for the semihydrogenation of 1a,
see Supporting Information.
(10) See Supporting Information for details.
(11) (a) Derrien, M. L. Catalytic Hydrogenation, Stud. Surf. Sci. Catal.,
Vol. 27 (Ed.: L. Červený), Elsevier, Amsterdam, 1986, p. 613. (b) Piringer,
O. G.; Baner, A. L. Plastic Packaging: Interactions with Food and Phar-
maceuticals 2nd ed., Wiley-VCH, 2008.
(12) For examples of Pd-catalyzed semihydrogenation of alkynes, see: (a)
van Laren, M. W.; Elsevier, C. J. Angew. Chem. Int. Ed. 1999, 38, 3715. (b)
Yabe, Y.; Yamada, T.; Nagata, S.; Sawama, Y.; Monguchi, Y.; Sajiki, H.;
Adv. Synth. Catal. 2012, 354, 1264. (c) Mitsudome, T.; Takahashi, Y.;
Ichikawa, S.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Angew. Chem. Int.
Ed. 2013, 52, 1481.
(13) (a) Armbrüster, M.; Kovnir, K.; Friedrich, M.; Teschner, D.;
Wowsnick, G.; Hahne, M.; Gille, P.; Szentmiklósi, L.; Feuerbacher, M.;
Heggen, M.; Girgsdies, F.; Rosenthal, D.; Schlögl, R.; Grin, Yu. Nat. Mater.
2
012, 11, 690. (b) Torres Galvis, H. M.; Bitter, J. H.; Khare, C. B.; Ruit-
enbeek, M.; Dugulan, A. I.; de Jong, K. P. Science 2012, 335, 835.
14) (a) Brown, C. A.; Ahuja, V. K.; J. Chem. Soc. Chem. Commun. 1973,
53. (b) Studt, F.; Abild-Pedersen, F.; Bligaard, T.; Sørensen, R. Z.; Chris-
tensen, C. H.; Nørskov, J. K. Science 2008, 320, 1320. (c) Carenco, S.;
(
5
ACS Paragon Plus Environment