CuI/2, 2'-Bipyridine/2, 2, 6, 6-Tetramethylpiperidinooxy Catalytic Oxidation Process of Alcohol to Nitrile
- Corresponding author: CAO Zubin, caozubin974@163.com
Citation:
XU Kunlun, CAO Zubin, QIAO Haiyan, HAN Dongyun, SHI Weiwei. CuI/2, 2'-Bipyridine/2, 2, 6, 6-Tetramethylpiperidinooxy Catalytic Oxidation Process of Alcohol to Nitrile[J]. Chinese Journal of Applied Chemistry,
;2018, 35(11): 1335-1341.
doi:
10.11944/j.issn.1000-0518.2018.11.170446
Lee G A, Freedman H H. Phase Transfer Catalyzed Oxidations of Alcohols and Amines by Aqueous Hypochlorite[J]. Tetrahedron Lett, 1976,17(20):1641-1644. doi: 10.1016/S0040-4039(00)92911-3
Miller J S, Manson J L. Designer Magnets Containing Cyanides and Nitriles[J]. Acc Chem Res, 2001,34(7):563-570. doi: 10.1021/ar0000354
Smith M B, March J. March's Advanced Organic Chemistry:Reactions, Mechanisms, and Structure, Sixth Edition[J]. Molecules, 2006,6(12):1064-1065.
Fleming F F, Yao L, Ravikumar P C. Nitrile-containing Pharmaceuticals:Efficacious Roles of the Nitrile Pharmacophore[J]. J Med Chem, 2010,53(22):7902-7917. doi: 10.1021/jm100762r
Trumm S, Wipff G, Geist A. Optimising BTP Ligands by Tuning Their Basicity[J]. Radiochim Acta, 2011,99(1):13-16. doi: 10.1524/ract.2011.1794
Tamilselvan P, Basavaraju Y B, Sampathkumar E. Cobalt(Ⅱ) Catalyzed Dehydration of Aldoximes:A Highly Efficient Practical Procedure for the Synthesis of Nitriles[J]. Catal Commun, 2009,10(5):716-719. doi: 10.1016/j.catcom.2008.11.025
Ghorbani-Vaghei R, Shiri L, Ghorbani-Choghamarani A. An Efficient, Rapid and Facile Procedure for Conversion of Aldoximes to Nitriles Using Triphenylphosphine and N-Halo Sulfonamides[J]. Chinese Chem Lett, 2013,24(12):1123-1126. doi: 10.1016/j.cclet.2013.07.020
Tang X, An J, Denton R M. A Procedure for Appel Halogenations and Dehydrations Using a Polystyrene Supported Phosphine Oxide[J]. Tetrahedron Lett, 2014,55(4):799-802. doi: 10.1016/j.tetlet.2013.11.098
Shu Z, Ye Y, Deng Y. Palladium(Ⅱ)-Catalyzed Direct Conversion of Methyl Arenes into Aromatic Nitriles[J]. Angew Chem Int Ed, 2013,52(40):10573-10576. doi: 10.1002/anie.201305731
Jasem Y A, Barkhad M, Khazali M A. Two Ways of Preparing Benzonitriles Using BrCCl3-PPh3 as the Reagent[J]. J Chem Res, 2014,38(2):80-84. doi: 10.3184/174751914X13891131118347
Biondini D, Brinchi L, Germani R. Dehydrogenation of Amines to Nitriles in Aqueous Micelles[J]. Eur J Org Chem, 2005,2005(14):3060-3063. doi: 10.1002/(ISSN)1099-0690
Kim J, Chang S. A New Combined Source of "CN" from N, N-Dimethylformamide and Ammonia in the Palladium-Catalyzed Cyanation of Aryl C-H Bonds[J]. J Am Chem Soc, 2010,132(30):10272-10274. doi: 10.1021/ja104917t
Lamani M, Prabhu K R. An Efficient Oxidation of Primary Azides Catalyzed by Copper Iodide:A Convenient Method for the Synthesis of Nitriles[J]. Angew Chem Int Ed, 2010,49(37):6622-6625. doi: 10.1002/anie.201002635
Rokade B V, Malekar S K, Prabhu K R. A Novel Oxidative Transformation of Alcohols to Nitriles:An Efficient Utility of Azides as a Nitrogen Source[J]. Chem Commun, 2012,48(44):5506-5508. doi: 10.1039/c2cc31256e
Oishi T, Yamaguchi K, Mizuno N. Catalytic Oxidative Synthesis of Nitriles Directly from Primary Alcohols and Ammonia[J]. Angew Chem Int Ed, 2009,48(34):6286-6288. doi: 10.1002/anie.200900418
Yamaguchi K, He J, Oishi T. The "Borrowing Hydrogen Strategy" by Supported Ruthenium Hydroxide Catalysts:Synthetic Scope of Symmetrically and Unsymmetrically Substituted Amines[J]. Chem-Eur J, 2010,16(24):7199-7207. doi: 10.1002/chem.201000149
Nie R, Shi J, Xia S. MnO2/Graphene Oxide:A Highly Active Catalyst for Amide Synthesis from Alcohols and Ammonia in Aqueous Media[J]. J Mater Chem, 2012,22(35):18115-18118. doi: 10.1039/c2jm34652d
Ishida T, Watanabe H, Takei T. Metal Oxide-catalyzed Ammoxidation of Alcohols to Nitriles and Promotion Effect of Gold Nanoparticles for One-Pot Amide Synthesis[J]. Appl Catal, A, 2012,425:85-90.
Dornan L M, Cao Q, Flanagan J C A. Copper/TEMPO Catalysed Synthesis of Nitriles from Aldehydes or Alcohols Using Aqueous Ammonia and with Air as the Oxidant[J]. Chem Commun, 2013,49(54):6030-6032. doi: 10.1039/c3cc42231c
Tao C, Liu F, Zhu Y. Copper-catalyzed Aerobic Oxidative Synthesis of Aryl Nitriles from Benzylic Alcohols and Aqueous Ammonia[J]. Org Biomol Chem, 2013,11(20):3349-3354. doi: 10.1039/c3ob00002h
Dighe S U, Chowdhury D, Batra S. Iron Nitrate/TEMPO:A Superior Homogeneous Catalyst for Oxidation of Primary Alcohols to Nitriles in Air[J]. Adv Synth Catal, 2014,356(18):3892-3896. doi: 10.1002/adsc.v356.18
Yin W, Wang C, Huang Y. Highly Practical Synthesis of Nitriles and Heterocycles from Alcohols Under Mild Conditions by Aerobic Double Dehydrogenative Catalysis[J]. Org Lett, 2013,15(8):1850-1853. doi: 10.1021/ol400459y
Zhang Y, Huang R, Gao B. Solvent-Free Aerobic Oxidation of Alcohols to Nitriles Catalyzed by Copper Iodide in Combination with a Quaternary Ammonium Modified TEMPO[J]. Catal Lett, 2016,146(1):220-228. doi: 10.1007/s10562-015-1634-0
Jagadeesh R V, Junge H, Beller M. Green Synthesis of Nitriles Using Non-Noble Metal Oxides-based Nanocatalysts[J]. Nat Commun, 2014,5:4123-4130. doi: 10.1038/ncomms5123
Osterberg P M, Niemeier J K, Welch C J. Experimental Limiting Oxygen Concentrations for Nine Organic Solvents at Temperatures and Pressures Relevant to Aerobic Oxidations in the Pharmaceutical Industry[J]. Org Process Res Dev, 2014,19(11):1537-1543.
Rogan L, Hughes N L, Cao Q. Copper(Ⅰ)/ketoABNO Catalysed Aerobic Alcohol Oxidation[J]. Catal Sci Technol, 2014,4(6):1720-1725. doi: 10.1039/C4CY00219A
Hoover J M, Ryland B L, Stahl S S. Copper/TEMPO-Catalyzed Aerobic Alcohol Oxidation:Mechanistic Assessment of Different Catalyst Systems[J]. ACS Catal, 2013,3(11):2599-2605. doi: 10.1021/cs400689a
Zhang G, Zhang G, Lei J. Aerobic Alcohol Ammoxidation Catalyzed by Copper(Ⅰ)/Amino Acid:A Scalable Protocol to Nitriles[J]. Chem Res Chinese Univ, 2016,32(4):586-593. doi: 10.1007/s40242-016-6067-9
Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
Yongmei Liu , Lisen Sun , Zhen Huang , Tao Tu . Curriculum-Based Ideological and Political Design for the Experiment of Methanol Oxidation to Formaldehyde Catalyzed by Electrolytic Silver. University Chemistry, 2024, 39(2): 67-71. doi: 10.3866/PKU.DXHX202308020
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
Hailian Tang , Siyuan Chen , Qiaoyun Liu , Guoyi Bai , Botao Qiao , Fei Liu . Stabilized Rh/hydroxyapatite Catalyst for Furfuryl Alcohol Hydrogenation: Application of Oxidative Strong Metal-Support Interactions in Reducing Conditions. Acta Physico-Chimica Sinica, 2025, 41(4): 100036-. doi: 10.3866/PKU.WHXB202408004
Tao Cao , Fang Fang , Nianguang Li , Yinan Zhang , Qichen Zhan . Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates. University Chemistry, 2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098
Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO3/SiO2. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
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 CuOx/TiO2 Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-. doi: 10.3866/PKU.WHXB202408015
Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
Ronghao Zhao , Yifan Liang , Mengyao Shi , Rongxiu Zhu , Dongju Zhang . Investigation into the Mechanism and Migratory Aptitude of Typical Pinacol Rearrangement Reactions: A Research-Oriented Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 305-313. doi: 10.3866/PKU.DXHX202309101
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
Yiling Wu , Peiyao Jin , Shenyue Tian , Ji Zhang . The Star of Sugar Substitutes: An Interview of Erythritol. University Chemistry, 2024, 39(9): 22-27. doi: 10.12461/PKU.DXHX202404034
Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
Junke LIU , Kungui ZHENG , Wenjing SUN , Gaoyang BAI , Guodong BAI , Zuwei YIN , Yao ZHOU , Juntao LI . Preparation of modified high-nickel layered cathode with LiAlO2/cyclopolyacrylonitrile dual-functional coating. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1461-1473. doi: 10.11862/CJIC.20240189
Xinhao Yan , Guoliang Hu , Ruixi Chen , Hongyu Liu , Qizhi Yao , Jiao Li , Lingling Li . Polyethylene Glycol-Ammonium Sulfate-Nitroso R Salt System for the Separation of Cobalt (II). University Chemistry, 2024, 39(6): 287-294. doi: 10.3866/PKU.DXHX202310073
Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO2-0.39IrOx composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
Kai CHEN , Fengshun WU , Shun XIAO , Jinbao ZHANG , Lihua ZHU . PtRu/nitrogen-doped carbon for electrocatalytic methanol oxidation and hydrogen evolution by water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1357-1367. doi: 10.11862/CJIC.20230350
Zhuo WANG , Junshan ZHANG , Shaoyan YANG , Lingyan ZHOU , Yedi LI , Yuanpei LAN . Preparation and photocatalytic performance of CeO2-reduced graphene oxide by thermal decomposition. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1708-1718. doi: 10.11862/CJIC.20240067
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
Zijian Jiang , Yuang Liu , Yijian Zong , Yong Fan , Wanchun Zhu , Yupeng Guo . Preparation of Nano Zinc Oxide by Microemulsion Method and Study on Its Photocatalytic Activity. University Chemistry, 2024, 39(5): 266-273. doi: 10.3866/PKU.DXHX202311101
Zhuoya WANG , Le HE , Zhiquan LIN , Yingxi WANG , Ling LI . Multifunctional nanozyme Prussian blue modified copper peroxide: Synthesis and photothermal enhanced catalytic therapy of self-provided hydrogen peroxide. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2445-2454. doi: 10.11862/CJIC.20240194