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aerobic oxidative dehydrogenation) of 4 proceeds to give the
corresponding N‐cyclohexylaniline (2) as the final product with the
concurrent formation of 1 and dicyclohexylamine (5) (step 3 in
Scheme 2). In the aromatization step, 13, 4, and/or molecular
Frey and B. Plietker, Chem. – Eur. J., 2013, 19, 2741; (f) X. Cui, X.
DOI: 10.1039/C5CC06514C
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Santoro, R. Psaro, N. Ravasio and F. Zaccheria, RSC Adv., 2014, 4,
2596.
1
5
oxygen can act as the hydrogen acceptors. Amines 1 and 5 formed
in the aromatization step are again aerobically oxidized by gold
7
(a) R. Apodaca and W. Xiao, Org. Lett., 2001, 3, 1745; (b) O.‐Y.
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(
steps 1 and 4 in Scheme 2). Concequently, it can be considered
that molecular oxygen is formally the terminal oxidant in the
present tandem oxidation processes. As above‐mentioned, the
cis/trans ratios of the products were slightly different from those of
the substrates for the transformation of substituted
cyclohexylamines. This is likely due to the disproportionation of 4
(step 3 in Scheme 2) and the oxidation of 5 (step 4 in Scheme 2).
The successive oxidative aromatization of N‐cyclohexylaniline to
8
9
(a) F. Paul, J. Patt and J. F. Hartwig, J. Am. Chem. Soc., 1994, 116,
diphenylamine is possibly proceeds through the similar way.
We thank Mr. H. Oshikawa (The University of Tokyo) for his help
with HAADF‐STEM and EDS analyses. This work was supported in
part by Grants‐in‐Aid for Scientific Researches from Ministry of
Education, Culture, Sports, Science and Technology in Japan (MEXT).
A part of this work was conducted in Research Hub for Advanced
Nano Characterization, The University of Tokyo, under the support
of ‘‘Nanotechnology platform’’ (project No. 12024043, MEXT). K. T.
was supported by Japan Society for the Promotion of Science
through Program for Leading Graduate Schools (MERIT Program)
and Research Fellowship for Young Scientists.
5
969; (b) A. S. Guram and S. L. Buchwald, J. Am. Chem. Soc.,
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1 (a) S. A. Girard, X. Hu, T. Knauber, F. Zhou, M.‐O. Simon, G.‐J.
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3 The average size of gold–palladium alloy nanoparticles in the
2
fresh Au–Pd/Al O was 1.7 nm and increased to 4.6 nm after the
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1
4 Although Pd/Al O could catalyze the transformations in
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2
3
Ar
1
5 Under
atmosphere,
the
Au–Pd/Al O ‐catalyzed
2 3
transformation of 10 gave a 1:2 mixture of 11 and 12
(
2 3
Scheme S2, ESi†). Considering the results of Au–Pd/Al O ‐
catalyzed transformation of 10 under aerobic and anaerobic
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4
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