Copper-catalyzed aerobic conversion of the CO bond of ketones to a CN bond using ammonium salts as the nitrogen source
作者： Bin Xu , Qing Jiang , An Zhao , Jing Jia , Qiang Liu
DOI: 10.1039/C5CC02578H
关键词: Nitrogen source 、 Copper 、 Catalysis 、 Ammonium 、 Chemistry 、 Molecular oxygen 、 Inorganic chemistry 、 Polymer chemistry 、 Copper catalyzed
摘要: The conversion of the CO bond ketones to a CN is described. This catalyzed by copper salts with ammonium as nitrogen source in presence molecular oxygen. A wide variety can be converted into corresponding compounds containing bond. Based on preliminary experiments, plausible mechanism this transformation disclosed.
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sci-hub.se 参考文章(30)
Richard C. Larock, Comprehensive organic transformations : a guide to functional group preparations Wiley-VCH. ,(2018) , 10.1002/9781118662083
Kotaro Miyagi, Katsuhiko Moriyama, Hideo Togo, One‐Pot Transformation of Carboxylic Acids into Nitriles European Journal of Organic Chemistry. ,vol. 2013, pp. 5886- 5892 ,(2013) , 10.1002/EJOC.201300629
Shashikant U Dighe, Deepan Chowdhury, Sanjay Batra, None, Iron Nitrate/TEMPO: a Superior Homogeneous Catalyst for Oxidation of Primary Alcohols to Nitriles in Air Advanced Synthesis & Catalysis. ,vol. 356, pp. 3892- 3896 ,(2014) , 10.1002/ADSC.201400718
Xiaoqiang Huang, Xinyao Li, Miancheng Zou, Song Song, Conghui Tang, Yizhi Yuan, Ning Jiao, From ketones to esters by a Cu-catalyzed highly selective C(CO)-C(alkyl) bond cleavage: aerobic oxidation and oxygenation with air. Journal of the American Chemical Society. ,vol. 136, pp. 14858- 14865 ,(2014) , 10.1021/JA5073004
Virgilio P. Gozum, Robert C. Mebane, Solvent-free and atom efficient conversion of aldehydes into nitriles Green Chemistry Letters and Reviews. ,vol. 6, pp. 149- 150 ,(2013) , 10.1080/17518253.2012.728633
Lijun Gu, Cheng Jin, Copper-catalyzed aerobic oxidative cleavage of C-C bonds in epoxides leading to aryl nitriles and aryl aldehydes. Chemical Communications. ,vol. 51, pp. 6572- 6575 ,(2015) , 10.1039/C5CC00360A
David Cantillo, C. Oliver Kappe, Direct preparation of nitriles from carboxylic acids in continuous flow. Journal of Organic Chemistry. ,vol. 78, pp. 10567- 10571 ,(2013) , 10.1021/JO401945R
Shaolin Zhou, Kathrin Junge, Daniele Addis, Shoubhik Das, Matthias Beller, A General and Convenient Catalytic Synthesis of Nitriles from Amides and Silanes Organic Letters. ,vol. 11, pp. 2461- 2464 ,(2009) , 10.1021/OL900716Q
M. B. Madhusudana Reddy, M. A. Pasha, Efficient and High-Yielding Protocol for the Synthesis of Nitriles from Aldehydes Synthetic Communications. ,vol. 40, pp. 3384- 3389 ,(2010) , 10.1080/00397910903419894
Laura M. Dornan, Qun Cao, James C. A. Flanagan, James J. Crawford, Matthew J. Cook, Mark J. Muldoon, Copper/TEMPO catalysed synthesis of nitriles from aldehydes or alcohols using aqueous ammonia and with air as the oxidant. Chemical Communications. ,vol. 49, pp. 6030- 6032 ,(2013) , 10.1039/C3CC42231C