Ruthenium-Catalyzed Direct Methylation of Primary and Secondary Aromatic Amines Using Carbon Dioxide and Molecular Hydrogen

被引:221
作者
Beydoun, Kassem [1 ]
vom Stein, Thorsten [1 ]
Klankermayer, Juergen [1 ]
Leitner, Walter [1 ,2 ]
机构
[1] Rhein Westfal TH Aachen, Inst Tech & Makromol Chem, D-52074 Aachen, Germany
[2] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
carbon dioxide; homogeneous catalysis; hydrogenation; methylation; ruthenium; NMR-SPECTROSCOPY; HOMOGENEOUS HYDROGENATION; FORMIC-ACID; CO2; METHANOL; LIGANDS; TRANSFORMATION; CHEMISTRY; RELEVANCE; FORMATES;
D O I
10.1002/anie.201304656
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The effective catalytic N-methylation of anilines using CO2 as C1 source and molecular hydrogen as reducing agent was demonstrated using the well-defined [Ru(triphos)(tmm)] catalyst. Secondary and primary (shown) aromatic amines were mono- or dialkylated, respectively, in high yields. N-methylation of amides coupled with the amide hydrogenation offers an efficient approach to unsymmetrical tertiary methyl/alkyl/aromatic amines. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:9554 / 9557
页数:4
相关论文
共 54 条
[1]  
[Anonymous], 1995, Angew. Chem., DOI DOI 10.1002/ANGE.19951072005
[2]   Catalysis research of relevance to carbon management: Progress, challenges, and opportunities [J].
Arakawa, H ;
Aresta, M ;
Armor, JN ;
Barteau, MA ;
Beckman, EJ ;
Bell, AT ;
Bercaw, JE ;
Creutz, C ;
Dinjus, E ;
Dixon, DA ;
Domen, K ;
DuBois, DL ;
Eckert, J ;
Fujita, E ;
Gibson, DH ;
Goddard, WA ;
Goodman, DW ;
Keller, J ;
Kubas, GJ ;
Kung, HH ;
Lyons, JE ;
Manzer, LE ;
Marks, TJ ;
Morokuma, K ;
Nicholas, KM ;
Periana, R ;
Que, L ;
Rostrup-Nielson, J ;
Sachtler, WMH ;
Schmidt, LD ;
Sen, A ;
Somorjai, GA ;
Stair, PC ;
Stults, BR ;
Tumas, W .
CHEMICAL REVIEWS, 2001, 101 (04) :953-996
[3]  
Aresta M., 2010, CARBON DIOXIDE CHEM
[4]  
Balaraman E, 2011, NAT CHEM, V3, P609, DOI [10.1038/NCHEM.1089, 10.1038/nchem.1089]
[5]  
Behr A., 1988, CARBON DIOXIDE ACTIV
[6]   TRIPODAL POLYPHOSPHINE LIGANDS CONTROL SELECTIVITY OF ORGANOMETALLIC REACTIONS [J].
BIANCHINI, C ;
MELI, A ;
PERUZZINI, M ;
VIZZA, F ;
ZANOBINI, F .
COORDINATION CHEMISTRY REVIEWS, 1992, 120 :193-208
[7]   A tripodal sulfur ligand for the selective ruthenium-catalysed hydrogenation of dimethyl oxalate [J].
Boardman, Brian ;
Hanton, Martin J. ;
van Rensburg, Hendrik ;
Tooze, Robert P. .
CHEMICAL COMMUNICATIONS, 2006, (21) :2289-2291
[8]  
Clarke H. T., 1933, J. Am. Chem. Soc, V55, P4571, DOI 10.1021/ja01338a041
[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]  
Cokoja M., 2011, ANGEW CHEM, V123, P8662, DOI DOI 10.1002/ANGE.201102010