Abstract
Gold clusters and nanoparticles were deposited on the three kinds of porous coordination polymers (PCP5), MOF-5, CPL-2, and AI-MIL53 by the solid grinding method. The size of Au particles depended on the kinds of PCPs and increased in the order of AI-MIL53 < CPL-2 < MOF-5. The mean diameter of Au particles supported on AI-MIL53 was estimated to be 1.6 nm by HAADFSTEM. Such small Au clusters on AI-MIL53 can catalyze one-pot synthesis of secondary amines from primary amines by sequential oxidation/hydrogenation owing to the remarkable improvement of hydrogenation efficiency of imine. Gold clusters deposited on AI-MIL53 can also promoteN-alkylation of amine with alcohol to form a secondary amine under N2 atmosphere without using O2 and H2.
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References
M. Haruta,Chem. Rec. 2003,3, 75–87
T. Ishida, M. Haruta,Angew. Chem. Int. Ed. 2007,46, 7154–7156
H. Miyamura, R. Matsubara, Y. Miyazaki, S. Kobayashi,Angew. Chem. Int. Ed. 2007,46, 4151–4154
S. Kanaoka, N. Yagi, Y. Fukuyama, S. Aoshima, H. Tsunoyama, T. Tsukuda, H. Sakurai,J. Am. Chem. Soc. 2007,129, 12060–12061
A. Biffis, S. Cunial, P. Spontoni, L. Prati,J. Catal. 2007,251, 1–6
T. Ishida, S. Okamoto, R. Makiyama, M. Haruta,Appl. Catal. A: Gen. 2009,353, 243–248
S. Hermes, M.K. Schröter R. Schmid, L. Khodeir, M. Muhler, A. Tissler, R.W. Fischer, R.A. Fische,Angew. Chem. Int. Ed. 2005,44, 6237–6241
M. Sabo, A. Henschel, H. Fröde, E. Klemm, S. Kaskel,J. Mater. Chem. 2007,17, 3827–3832
F. Schröder, D. Esken, M. Cokoja, M.W.E. van den Berg, O.I. Lebede, G. Van Tendeloo, B. Walaszek, G. Buntkowsky, H.H. Limbach, B. Chaudret, R.A. Fischer,J. Am. Chem. Soc. 2008,130, 6119–6130
T. Ishida, M. Nagaoka, T. Akita, M. Haruta,Chem. Eur. J. 2008,14, 8456–8460
H.L. Jiang, B. Liu, T. Akita, M. Haruta, H. Sakurai, Q. Xu,J. Am. Chem. Soc. 2009,131, 11302–11303
A. Grirrane, A. Corma, H. Garcia,J. Catat 2009,264, 138–144
H. Sun, F.Z. Su, J. Ni, Y. Cao, H.Y. He, K.N. Fan,Angew. Chem. Int. Ed. 2009,48, 4390–4393
N.A. Ramsahye, G. Maurin, S. Bourrelly, P. Llewellyn, T. Loiseau, G. Ferey,Phys. Chem. Chem. Phys. 2007,9, 1059–1063
H. Li, M. Eddaoudi, M. O’Keeffe, O.M. Yaghi,Nature 1999,402, 276–279
M. Kondo, T. Okubo, A. Asami, S.I. Noro, T. Yoshitomi, S. Kitagawa,Angew. Chem. Int. Ed. 1999,38, 140–143
S. Tsubota, M. Haruta, T. Kobayashi, A. Ueda, Y. Nakahara,Stud. Surf. Sci. Catal. 1991,63, 695–704
B. Zhu, M. Lazar, B.G. Trewyn, R.J. Angelici,J. Catal. 2008,260, 1–6
A. Grirrane, A. Corma, H. Garcia,Science 2008,322, 1661–1664
F. Bus, J.T. Miller, J.A. Van Bokhoven,J. Phys. Chem. B 2005,109, 14581–14587
A. Abad, A. Corma, H. Garcia,Chem. Eur J. 2008,14, 212–222
P. Fristrup, L.B. Johansen, C.H. Christensen,Chem. Commun. 2008, 2750–2752
M. Conte, H. Miyamura, S. Kobayashi, V. Chechik,J. Am. Chem. Soc. 2009,131, 7189–7196
F.Z. Su, L. He, J. Ni, Y. Cao, H.Y. He, K.N. Fan,Chem. Commun. 2008, 3531–3533
L.L. Santos, P. Serna, A. Corma,Chem. Eur. J. 2009,15, 8196–8203
Shimizu et al. have very recently reported theN-alkylation of benzylalcohol over Ag/Al2O3 and Au/Al2O3 in the co-presence of FeCl3 · 6H2O. In this case, the aid of FeCl3 and Al2O3 are required to obtain secondary amine; K-I. Shimizu, M. Nishimura, A. Satsuma,ChemCatChem 2009,1, 497–503
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Tamao Ishida received PhD from Kyoto University in March, 2006. After JSPS post-doctoral fellow at Kyoto University, in August 2006, she joined Prof. Haruta’s group of Tokyo Metropolitan University as an assistant professorNoriko Kawakita is now a master course student at the Department of Applied Chemistry, Tokyo Metropolitan University, Japan.
Tomoki Akita received PhD from Osaka University in 1998. After working as a post-doctoral researcher at Osaka National Research Institute (ONRI, currently AIST), he obtained a researcher position at ONRI in 1999. He is now a senior research scientist at the Research Institute for Ubiquitous Energy Devices, AIST
Masatake Haruta received PhD from Kyoto University in 1976, when he was offered a researcher position at ONRI. In 2001, he moved to Tsukuba as the director of the Research Institute for Green Technology, AIST. In 2005, he was appointed as a professor at Tokyo Metropolitan University
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Ishida, T., Kawakita, N., Akita, T. et al. One-potN-alkylation of primary amines to secondary amines by gold clusters supported on porous coordination polymers. Gold Bull 42, 267–274 (2009). https://doi.org/10.1007/BF03214948
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DOI: https://doi.org/10.1007/BF03214948