Green and Practical Oxidative Deoximation of Oximes to Ketones or Aldehydes with Hydrogen Peroxide/Air by Organoselenium Catalysis

作者: Xiaobi Jing , Dandan Yuan , Lei Yu

DOI: 10.1002/ADSC.201601353

关键词: Oxidative phosphorylationOrganic chemistryHydrogen peroxideChemistryCatalysisSelenium

摘要: Organoselenium-catalyzed oxidative deoximations afforded ketones and aldehydes under mild conditions. The reactions employ hydrogen peroxide air as clean oxidants lead to a waste-free metal-free deprotection protocol for carbonyl protection strategies well the green synthesis of aldehydes. mechanisms this interesting organoselenium-catalyzed reaction have been investigated by control experiments selenium 77 nuclear magnetic resonance (77Se NMR) tests. This novel largely expands application scope organoselenium catalysis.

参考文章(58)
Jie Luo, Zechen Zhu, Yannan Liu, Xiaodan Zhao, Diaryl Selenide Catalyzed Vicinal Trifluoromethylthioamination of Alkenes Organic Letters. ,vol. 17, pp. 3620- 3623 ,(2015) , 10.1021/ACS.ORGLETT.5B01727
Lei Yu, Jun Wang, Tian Chen, Kehong Ding, Yi Pan, 二苯基二硒醚催化双氧水氧化环己烯合成1,2-环己二醇 Chinese Journal of Organic Chemistry. ,vol. 33, pp. 1096- 1099 ,(2013) , 10.6023/CJOC2012012049
Luca Sancineto, Caterina Tidei, Luana Bagnoli, Francesca Marini, Eder Lenardão, Claudio Santi, Selenium Catalyzed Oxidation of Aldehydes: Green Synthesis of Carboxylic Acids and Esters Molecules. ,vol. 20, pp. 10496- 10510 ,(2015) , 10.3390/MOLECULES200610496
Lei Yu, Jianqing Ye, Xu Zhang, Yuanhua Ding, Qing Xu, Recyclable (PhSe)2-catalyzed selective oxidation of isatin by H2O2: a practical and waste-free access to isatoic anhydride under mild and neutral conditions Catalysis Science & Technology. ,vol. 5, pp. 4830- 4838 ,(2015) , 10.1039/C5CY01030F
FC Meotti, VC Borges, G Zeni, JBT Rocha, CW Nogueira, Potential renal and hepatic toxicity of diphenyl diselenide, diphenyl ditelluride and Ebselen for rats and mice. Toxicology Letters. ,vol. 143, pp. 9- 16 ,(2003) , 10.1016/S0378-4274(03)00090-0
Diana M. Freudendahl, Stefano Santoro, Sohail A. Shahzad, Claudio Santi, Thomas Wirth, Grüne Chemie mit Selenreagentien: Entwicklung effizienter katalytischer Reaktionen Angewandte Chemie. ,vol. 121, pp. 8559- 8562 ,(2009) , 10.1002/ANGE.200903893
Helmut Duddeck, Selenium-77 nuclear magnetic resonance spectroscopy Progress in Nuclear Magnetic Resonance Spectroscopy. ,vol. 27, pp. 1- 323 ,(1995) , 10.1016/0079-6565(94)00005-F
Avelino Corma, Pedro Serna, Hermenegildo García, Gold Catalysts Open a New General Chemoselective Route to Synthesize Oximes by Hydrogenation of α,β-Unsaturated Nitrocompounds with H2 Journal of the American Chemical Society. ,vol. 129, pp. 6358- 6359 ,(2007) , 10.1021/JA0704131
Wendy A. Loughlin, Joel D. A. Tyndall, Matthew P. Glenn, Timothy A. Hill, David P. Fairlie, Update 1 of: Beta-Strand Mimetics Chemical Reviews. ,vol. 110, pp. 1- 38 ,(2010) , 10.1021/CR900395Y