N-methylation of quinolines with CO2 and H2 catalyzed by Ru-triphos complexes

被引:26
作者
He, Zhenhong [1 ,3 ]
Liu, Huizhen [1 ,2 ]
Qian, Qingli [1 ]
Lu, Lu [1 ]
Guo, Weiwei [1 ]
Zhang, Lujun [1 ]
Han, Buxing [1 ,2 ]
机构
[1] Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Colloid & Interface & Thermodynam, Inst Chem, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Shaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Xian 710021, Peoples R China
基金
中国国家自然科学基金;
关键词
methylation; hydrogenation; quinoline derivatives; carbon dioxide; homogeneous catalysis; SUPPORTED GOLD CATALYSTS; MILD REACTION CONDITIONS; CARBON-DIOXIDE; MOLECULAR-HYDROGEN; TETRAHYDROQUINOLINE ALKALOIDS; ASYMMETRIC-SYNTHESIS; ALLYLIC AMINATION; CARBOXYLIC-ACIDS; SECONDARY-AMINES; ANGUSTUREINE;
D O I
10.1007/s11426-017-9024-8
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
N-methyl-tetrahydroquinolines (MTHQs) are a kind of very useful chemicals, which can be obtained from N-methylation of amines. However, the methylation of quinolines which is a kind of highly unsaturated nitrogen-containing heterocyclic aromatic compounds has not been reported. In this work, we report the first work for the synthesis of MTHQs by methylation of quinolines using CO2 and H-2. It was found that Ru(acac)(3)-triphos [triphos: 1,1,1-tris(diphenylphosphinomethyl)ethanl] complex was very active and selective for the N-methylation reaction of quinolines, and the yield of the desired product could reach 99%.
引用
收藏
页码:927 / 933
页数:7
相关论文
共 54 条
[1]   An efficient one pot transfer hydrogenation and N-alkylation of quinolines with alcohols mediated by Pd/C/Zn [J].
Abarca, Belen ;
Adam, Rosa ;
Ballesteros, Rafael .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (09) :1826-1833
[2]   A facile one-pot synthesis of N-substituted tetrahydroquinolines [J].
Babu, Thelagathoti Hari ;
Shanthi, Gnanamani ;
Perumal, Paramasivan T. .
TETRAHEDRON LETTERS, 2009, 50 (24) :2881-2884
[3]   Conjugate Addition of Lithium N-Phenyl-N-(α-methylbenzyl)amide: Application to the Asymmetric Synthesis of (R)-(-)-Angustureine [J].
Bentley, Scott A. ;
Davies, Stephen G. ;
Lee, James A. ;
Roberts, Paul M. ;
Thomson, James E. .
ORGANIC LETTERS, 2011, 13 (10) :2544-2547
[4]   Ruthenium-Catalyzed Reductive Methylation of Imines Using Carbon Dioxide and Molecular Hydrogen [J].
Beydoun, Kassem ;
Ghattas, Ghazi ;
Thenert, Katharina ;
Klankermayer, Juergen ;
Leitner, Walter .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (41) :11010-11014
[5]   Carbon Dioxide Reduction to Methylamines under Metal-Free Conditions [J].
Blondiaux, Enguerrand ;
Pouessel, Jacky ;
Cantat, Thibault .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (45) :12186-12190
[6]  
Börjesson M, 2016, J AM CHEM SOC, V138, P7504, DOI [10.1021/jacs.6b04088, 10.1021/jacs.6604088]
[7]   Towards a general ruthenium-catalyzed hydrogenation of secondary and tertiary amides to amines [J].
Cabrero-Antonino, Jose R. ;
Alberico, Elisabetta ;
Junge, Kathrin ;
Junge, Henrik ;
Beller, Matthias .
CHEMICAL SCIENCE, 2016, 7 (05) :3432-3442
[8]   Selective Catalytic Hydrogenation of Heteroarenes with N-Graphene-Modified Cobalt Nanoparticles (Co3O4 Co/NGr@α-Al2O3) [J].
Chen, Feng ;
Surkus, Annette-Enrica ;
He, Lin ;
Pohl, Marga-Martina ;
Radnik, Jorg ;
Topf, Christoph ;
Junge, Kathrin ;
Beller, Matthias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (36) :11718-11724
[9]   Homogeneous Catalytic Hydrogenation of Amides to Amines [J].
Coetzee, Jacorien ;
Dodds, Deborah L. ;
Klankermayer, Juergen ;
Brosinski, Sandra ;
Leitner, Walter ;
Slawin, Alexandra M. Z. ;
Cole-Hamilton, David J. .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (33) :11039-11050
[10]   Direct Ruthenium-Catalyzed Hydrogenation of Carboxylic Acids to Alcohols [J].
Cui, Xinjiang ;
Li, Yuehui ;
Topf, Christoph ;
Junge, Kathrin ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (36) :10596-10599