Mendeleev Commun., 2014, 24, 332–333
Table 2 Synthesis of secondary amines via Aui-catalyzed hydroamination.
4 M. Boronat and A. Corma, J. Catal., 2011, 284, 138.
5 A. Corma, P. Concepcion, I. Dominguez, V. Fornes and M. J. Sabater,
J. Catal., 2007, 251, 39.
Entry
Alkyne
Amine
Product
Yielda (%)
6 X. Giner, C. Najera, G. Kovacs, A. Lledos and G. Ujaque, Adv. Synth.
Catal., 2011, 353, 3451.
7 T. E. Muller, K. C. Hultzsch, M. Yus, F. Foubelo and M. Tada, Chem.
1
1
1
1
1
1
5
5
5
5
7
7
2a
2b
2c
2d
2e
2b
2d
2f
4a
78
81
98
88
—
82
70
75
—
61
56
2
4b
3
4c
Rev., 2008, 108, 3795.
8 F. Alonso, I. P. Beletskaya and M. Yus, Chem. Rev., 2004, 104, 3079.
9 J. Seayad, A. Tillack, C. G. Hartung and M. Beller, Adv. Synth. Catal.,
2002, 344, 795.
4
4d
5
No reaction
6
6b
10 J. Zhao, Z. Zheng, S. Bottle, A. Chou, S. Sarina and H. Zhu, Chem.
7
6d
Commun., 2013, 49, 2676.
11 E. Mizushima, T. Hayashi and M. Tanaka, Org. Lett., 2003, 5, 3349.
12 V. Lavallo, G. D. Frey, B. Donnadieu, M. Soleilhavoup and G. Bertrand,
Angew. Chem. Int. Ed., 2008, 47, 5224.
8
6f
9
2g
2a
2b
No reaction
10
11
8a
8b
13 X. Zeng, G. D. Frey, S. Kousar and G. Bertrand, Chem. Eur. J., 2009,
15, 3056.
14 X. Zeng, G. D. Frey, R. Kinjo, B. Donnadieu and G. Bertrand, J. Am.
Chem. Soc., 2009, 131, 8690.
aYields after chromatographic isolation.
15 A. Leyva and A. Corma, Adv. Synth. Catal., 2009, 351, 2876.
16 C. Shu, L. Li, C.-B. Chen, H.-C. Shen and L.-W. Ye, Chem. Asian J.,
2014, 9, 1525.
17 J.-E. Kang and S. Shin, Synlett, 2006, 5, 717.
18 N. Senthilkumar, P. Gandeepan, J. Jayakumar and C.-H. Cheng, Chem.
Commun., 2014, 3106.
19 Q. Sun, Y. Wang, D. Yuan, Y. Yao and Q. Shen, Organometallics, 2014,
33, 994.
20 Q. Lei, Y. Wei, D. Talwar, C. Wang, D. Xue and J. Xiao, Chem. Eur. J.,
(entry 3), the use of a weak electron-withdrawing p-chloroaniline
2d also resulted in a high yield of product 4d (88%, entry 4).
However, in the case of stronger electron-withdrawing nitro-sub-
stituted reactant the reaction was completely cancelled (entry 5).
The presence of electron-donating methoxy group in alkyne 5
did not decrease its reactivity and amines 6b,d,f were isolated in
70–82% yields (entries 6–8). 3-Nitroaniline was essentially un-
reactive (entry 9). Aliphatic 1-heptyne 7 gave amines 8a,b in
lower yields, what is in good agreement with published data.15
The catalyst can be easily separated from product 4c by adding
hexane and can be used at least three times without substantial
loss in activity.
2013, 19, 4021.
21 W. Tang, C. Lau, X. Wu and J. Xiao, Synlett, 2014, 25, 81.
22 G. Ghattas, D. Chen, F. Pan and J. Klankermayer, Dalton Trans., 2012,
41, 9026.
23 N. Mrsic, L. Panella, E. G. IJpeij, A. J. Minnaard, B. L. Feringa and
J. G. de Vries, ChemCatChem, 2011, 3, 1139.
24 L. Rubio-Perez, F. J. Perez-Florez, P. Sharma, L. Velasco and A. Cabrera,
Org. Lett., 2009, 11, 265.
This work was supported by the Russian Science Foundation
(grant no. 14-23-00186).
25 C. Wang, A. Pettman, J. Bacsa and J. Xiao, Angew. Chem. Int. Ed., 2010,
49, 7548.
References
1 C. Della Pina, E. Faletta, L. Prati and M. Rossi, Chem. Soc. Rev., 2008,
37, 2077.
2 A. Corma and P. Serna, Nature, 2006, 313, 332.
3 A. A. Herzing, C. J. Kiely, A. F. Carley, P. Landon and G. J. Hutchings,
Science, 2008, 321, 1331.
Received: 13th October 2014; Com. 14/4483
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