Aerobic oxidative dehydrogenation of N-heterocycles catalyzed by cobalt porphyrin

被引:24
作者
Zhou, Weiyou [1 ]
Chen, Dongwei [1 ]
Sun, Fu'an [1 ]
Qian, Junfeng [1 ]
He, Mingyang [1 ]
Chen, Qun [1 ]
机构
[1] Changzhou Univ, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China
基金
美国国家科学基金会;
关键词
N-Heterocycles; Cobalt porphyrin; Oxidative dehydrogenation; No additive; NITROGEN-HETEROCYCLES; EFFICIENT CATALYST; ACCEPTORLESS DEHYDROGENATION; REVERSIBLE DEHYDROGENATION; AMINES; HYDROGENATION; NANOPARTICLES; ALCOHOLS; NANOHYBRID; CORROLES;
D O I
10.1016/j.tetlet.2018.01.094
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient catalytic procedure has been developed for the aerobic oxidative dehydrogenation of N-heterocycles by cobalt porphyrin in the absence of any additives. The catalytic system could tolerate various 1,2,3,4-tetrahydroquinoline derivatives and some other N-heterocycles. The corresponding N-heteroaromatics could be obtained in 59-86% yields. The mechanism investigation suggested that the aerobic oxidative dehydrogenation might proceed with imine intermediate through radical paths. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:949 / 953
页数:5
相关论文
共 37 条
[1]   A Molecular Iron Catalyst for the Acceptorless Dehydrogenation and Hydrogenation of N-Heterocycles [J].
Chakraborty, Sumit ;
Brennessel, William W. ;
Jones, William D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (24) :8564-8567
[2]   Selective functionalisation of saturated C-H bonds with metalloporphyrin catalysts [J].
Che, Chi-Ming ;
Lo, Vanessa Kar-Yan ;
Zhou, Cong-Ying ;
Huang, Jie-Sheng .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) :1950-1975
[3]   A High-Valent Iron-Oxo Corrolazine Activates C-H Bonds via Hydrogen-Atom Transfer [J].
Cho, Kevin ;
Leeladee, Pannee ;
McGown, Amanda J. ;
DeBeer, Serena ;
Goldberg, David P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (17) :7392-7399
[4]   Oxidation of secondary amines catalyzed by dirhodium caprolactamate [J].
Choi, Hojae ;
Doyle, Michael P. .
CHEMICAL COMMUNICATIONS, 2007, (07) :745-747
[5]   Selective C-H oxidation catalyzed by metalloporphyrins [J].
Costas, Miquel .
COORDINATION CHEMISTRY REVIEWS, 2011, 255 (23-24) :2912-2932
[6]   Synthesis and Characterization of Iron-Nitrogen-Doped Graphene/Core-Shell Catalysts: Efficient Oxidative Dehydrogenation of N-Heterocycles [J].
Cui, Xinjiang ;
Li, Yuehui ;
Bachmann, Stephan ;
Scalone, Michelangelo ;
Surkus, Annette-Enrica ;
Junge, Kathrin ;
Topf, Christoph ;
Beller, Matthias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (33) :10652-10658
[7]   Copper Nanoparticles from Copper Aluminum Hydrotalcite: An Efficient Catalyst for Acceptor- and Oxidant-Free Dehydrogenation of Amines and Alcohols [J].
Damodara, Dandu ;
Arundhathi, Racha ;
Likhar, Pravin R. .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (01) :189-198
[8]   An electrochemical and spectroelectrochemical study of pentacoordinated CoTPP on glassy carbon electrode [J].
De Paz, Heloise H. ;
Medard, Christelle ;
Morin, Mario .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2010, 648 (02) :163-168
[9]   Noncovalent nanohybrid of cobalt tetraphenylporphyrin with graphene for simultaneous detection of ascorbic acid, dopamine, and uric acid [J].
Deng, Keqin ;
Zhou, Jianhong ;
Li, Xiaofang .
ELECTROCHIMICA ACTA, 2013, 114 :341-346
[10]   Highly efficient aerobic oxidation of various amines using Pd3Pb intermetallic compounds as catalysts [J].
Furukawa, Shinya ;
Suga, Akifusa ;
Komatsu, Takayuki .
CHEMICAL COMMUNICATIONS, 2014, 50 (25) :3277-3280