Citation: 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 shu

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

1.
School of Chemical engineering, Guangdong University of Petrochemical Technology, Maoming, 525000

Corresponding author: Zhou Peng, zhoupeng@gdupt.edu.cn
Received Date: 15 January 2016
Revised Date: 16 March 2016

Fund Project: the Guangdong University of Petrochemical Technology No. 2015DCA037the National Natural Science Foundation of China No. 21272037the Natural Science Foundation of Guangdong Province No. S2013040014944

Figures(1)

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.
- Cu catalyzed,
- dioxygen,
- α-azoleketone,
- 2,2,6,6-tetramethylpiperidine-1-oxyl,
- α-aminoxylation
1. [1]
  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. [2]
  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. [3]
  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. [4]
  Wang, Z.-L.; An, X.-L.; Ge, L.-S.; Jin, J.-H.; Luo, X.; Deng, W.-P. Tetrahedron 2014, 70, 3788.
5. [5]
  Dinca, E.; Hartmann, P.; Smrček, 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. [6]
  Akagawa, K.; Fujiwara, T.; Sakamoto, S.; Kudo, K. Chem. Commun. 2010, 46, 8040.
7. [7]
  Bui, N.-N.; Ho, X.-H.; Mho, S.-I.; Jang, H.-Y. Eur. J. Org. Chem. 2009, 5309.
8. [8]
  Feng, P.; Song, S.; Zhang, L.-H.; Jiao, N. Synlett 2014, 25, 2717.
9. [9]
  Koike, T.; Yasu, Y.; Akita, M. Chem. Lett. 2012, 41, 999.
10. [10]
  Luo, X.; Wang, Z.-L.; Jin, J.-H.; An, X.-L.; Shen, Z.; Deng, W.-P. Tetrahedron 2014, 70, 8226.
11. [11]
  Li, Y.; Pouliot, M.; Vogler, T.; Renaud, P.; Studer, A. Org. Lett. 2012, 14, 4474.
12. [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. [13]
14. [14]
15. [15]
  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. [16]
  Kumar, D.; Reddy, V. B.; Kumar, A.; Mandal, D.; Tiwari, R.; Parang, K. Bioorg. Med. Chem. Lett. 2011, 21, 449.
1. [1]
  Pengzi Wang , Wenjing Xiao , Jiarong Chen . Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction. University Chemistry, 2025, 40(4): 239-244. doi: 10.12461/PKU.DXHX202406090
2. [2]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-. doi: 10.3866/PKU.WHXB202408015
3. [3]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
4. [4]
  Aiyi Xin , Jiawei Li , Xinyang Ran , Chuanjiang Fu , Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031
5. [5]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
6. [6]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
7. [7]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
8. [8]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
9. [9]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029
10. [10]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
11. [11]
  Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO₂-0.39IrO_x composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
12. [12]
  Xue Dong , Xiaofu Sun , Shuaiqiang Jia , Shitao Han , Dawei Zhou , Ting Yao , Min Wang , Minghui Fang , Haihong Wu , Buxing Han . 碳修饰的铜催化剂实现安培级电流电化学还原CO₂制C₂₊产物. Acta Physico-Chimica Sinica, 2025, 41(3): 2404012-. doi: 10.3866/PKU.WHXB202404012
13. [13]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
14. [14]
  Endong YANG , Haoze TIAN , Ke ZHANG , Yongbing LOU . Efficient oxygen evolution reaction of CuCo₂O₄/NiFe-layered bimetallic hydroxide core-shell nanoflower sphere arrays. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 930-940. doi: 10.11862/CJIC.20230369
15. [15]
  Yaping ZHANG , Tongchen WU , Yun ZHENG , Bizhou LIN . Z-scheme heterojunction β-Bi₂O₃ pillared CoAl layered double hydroxide nanohybrid: Fabrication and photocatalytic degradation property. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 531-539. doi: 10.11862/CJIC.20240256
16. [16]
  Ping ZHANG , Chenchen ZHAO , Xiaoyun CUI , Bing XIE , Yihan LIU , Haiyu LIN , Jiale ZHANG , Yu'nan CHEN . Preparation and adsorption-photocatalytic performance of ZnAl@layered double oxides. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1965-1974. doi: 10.11862/CJIC.20240014
17. [17]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
18. [18]
  Xin Han , Zhihao Cheng , Jinfeng Zhang , Jie Liu , Cheng Zhong , Wenbin Hu . Design of Amorphous High-Entropy FeCoCrMnBS (Oxy) Hydroxides for Boosting Oxygen Evolution Reaction. Acta Physico-Chimica Sinica, 2025, 41(4): 100033-. doi: 10.3866/PKU.WHXB202404023
19. [19]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
20. [20]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(857)
HTML views(102)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

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

Metrics

通讯作者: 陈斌, bchen63@163.com

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