Articles

Researches on the α-Aminoxylation between α-Azoleketones and 2,2,6,6-Tetramethylpiperidine-1-oxyl with Cu/O2

  • Zhou Peng ,
  • Qiu Huihua ,
  • Pan Hongcheng ,
  • Shi Jicheng ,
  • Zhou Jianmin
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  • School of Chemical engineering, Guangdong University of Petrochemical Technology, Maoming, 525000

Received date: 2016-01-15

  Revised date: 2016-03-16

  Online published: 2016-04-05

Supported by

Project supported by the National Natural Science Foundation of China (No. 21272037), the Natural Science Foundation of Guangdong Province (No. S2013040014944) and the Guangdong University of Petrochemical Technology (No. 2015DCA037).

Abstract

The α-aminoxylation between α-azoleketones and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) was studied in this paper. Taking Cu(II) salts as catalyst and air as oxidant, a number of alkoxyamines have been synthesized via α-aminoxylation between α-azoleketones and TEMPO in good yields at room temperature. This strategy is highlighted by appealing features such as mild reaction condition, inexpensive catalyst, green oxidant and good yield.

Cite this article

Zhou Peng , Qiu Huihua , Pan Hongcheng , Shi Jicheng , Zhou Jianmin . Researches on the α-Aminoxylation between α-Azoleketones and 2,2,6,6-Tetramethylpiperidine-1-oxyl with Cu/O2[J]. Chinese Journal of Organic Chemistry, 2016 , 36(7) : 1596 -1601 . DOI: 10.6023/cjoc201601019

References

[1] (a) Erdmann, A.; Menon, Y.; Gros, C.; Molinier, N.; Novosad, N.; Samson, A.; Gregoire, J.; Long, C.; Ausseil, F.; Hlby, L.; Arimondo, P. B. Bioorg. Med. Chem. 2015, 23, 5946
(b) Lanier, M.; Sergienko, E.; Simão A. M.; Su, Y.; Chung, T.; Millán, J. L.; Cashman, J. R. Bioorg. Med. Chem. 2010, 18, 573
(c) Salerno, L; Modica, M. N.; Romeo, G.; Pittalà, V.; Siracusa, M. A.; Amato, M. E.; Acquaviva, R.; Giacomo, C. D.; Sorrenti, V. Eur. J. Med. Chem. 2012, 49, 118
(d) Peifer, C.; Bühler, S.; Hauser, D.; Kinkel, K.; Totzke, F.; Schächtele, C.; Laufer, S. Eur. J. Med. Chem. 2009, 44, 1788
(e) Wei, Q.-L.; Zhang, S.-S.; Gao, J.; Li, W.-H.; Xu, L.-Z.; Yu, Z.-G. Bioorg. Med. Chem. 2006, 14, 7146
(f) Pautus, S.; Sehr, P.; Lewis, J.; Fortuné, A.; Wolkerstorfer, A.; Szolar, O.; Guilligay, D.; Lunardi, T.; Décout, J.-L.; Cusack, S. J. Med. Chem. 2013, 56, 8915.
[2] (a) Hawker, C. J.; Bosmann, A. W.; Harth, E. Chem. Rev. 2001, 101, 3661.
(b) Benoit, D.; Chaplinski, V.; Braslau, R.; Hawker, C. J. J. Am. Chem. Soc. 1999, 121, 3904.
[3] (a) Sciannamea V.; Jérôme, R.; Detrembleur C. Chem. Rev. 2008, 108, 1104.
(b) Calabrese, D. R.; Ditter, D.; Liedel, C.; Blumfield, A.; Zentel, R.; Ober, C. K. ACS Macro. Lett. 2015, 4, 606.
[4] Wang, Z.-L.; An, X.-L.; Ge, L.-S.; Jin, J.-H.; Luo, X.; Deng, W.-P. Tetrahedron 2014, 70, 3788.
[5] (a) Dinca, E.; Hartmann, P.; Smr?ek, J.; Dix, I.; Jones, P. G.; Jahn, U. Eur. J. Org. Chem. 2012, 4461.
(b) Kirchberg, S.; Fröhlich, R.; Studer, A. Angew. Chem., Int. Ed. 2010, 49, 6877.
(c) Abeykoon, G. A.; Chatterjee, S.; Chen, J. S. Org. Lett. 2014, 16, 3248.
[6] Akagawa, K.; Fujiwara, T.; Sakamoto, S.; Kudo, K. Chem. Commun. 2010, 46, 8040.
[7] Bui, N.-N.; Ho, X.-H.; Mho, S.-I.; Jang, H.-Y. Eur. J. Org. Chem. 2009, 5309.
[8] Feng, P.; Song, S.; Zhang, L.-H.; Jiao, N. Synlett 2014, 25, 2717.
[9] Koike, T.; Yasu, Y.; Akita, M. Chem. Lett. 2012, 41, 999.
[10] Luo, X.; Wang, Z.-L.; Jin, J.-H.; An, X.-L.; Shen, Z.; Deng, W.-P. Tetrahedron 2014, 70, 8226.
[11] Li, Y.; Pouliot, M.; Vogler, T.; Renaud, P.; Studer, A. Org. Lett. 2012, 14, 4474.
[12] Xie, Y.-X.; Song, R.-J.; Liu, Y.; Liu, Y.-Y.; Xiang, J.-N.; Li, J.-H. Adv. Synth. Catal. 2013, 355, 3387.
[13] Selected reviews on reaction via Cu-catalyzed single electron transfer: (a) McCann, S. D.; Stahl, S. S. Acc. Chem. Res. 2015, 48, 1756.
(b) Yu, H.; Su, S.; Chi, Z.; Dang, Z. -M. Chin. J. Org. Chem. 2013, 33, 1628 (in Chinese). (于海珠, 苏圣钦, 张弛, 党智敏, 有机化学, 2013, 33, 1628.)
[14] Selected reviews on Cu-catalyzed oxidation with molecular oxygen: (a) Punniyamurthy, T.; Velusamy, S.; Iqbal J. Chem. Rev. 2005, 105, 2329.
(b) Campbell, A. N.; Stahl, S. S. Acc. Chem. Res. 2012, 45, 851.
(c) Allen, S. E.; Walvoord, R. R.; Padilla-Salinas, R.; Kozlowski, M. C. Chem. Rev. 2013, 113, 6234
Some examples on Cu-catalyzed oxidation with molecular oxygen: (d) Gao, H.; Wang, H.; Huang, Z.; Yao, L.; Peng, J.; Chen, C. Chin. J. Org. Chem. 2015, 35, 1707 (in Chinese). (高翯, 王瀚旸, 黄章杰, 姚丽萍, 彭进松, 陈春霞, 有机化学, 2015, 35, 1707.)
(e) Li, J.; Zhang, Z.; Li, C.; Luo, W.; Yang, S. Chin. J. Org. Chem. 2015, 35, 2199 (in Chinese). (李建晓, 张振明, 李春生, 罗维, 杨少容, 有机化学, 2015, 35, 2199.)
[15] (a) Tsai, A. S.; Wilson, R. M.; Harada, H.; Berqman, R. G.; Ellman, J. A. Chem. Commun. 2009, 3910
(b) Zhang, Y.; Zhang, Y.; Xiao, J.; Peng, Z.; Dong, W.; An, D. Eur. J. Org. Chem. 2015, 35, 7806.
[16] Kumar, D.; Reddy, V. B.; Kumar, A.; Mandal, D.; Tiwari, R.; Parang, K. Bioorg. Med. Chem. Lett. 2011, 21, 449.

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