Selective Methylation of Amines with Carbon Dioxide and H2

被引:242
作者
Li, Yuehui [1 ]
Sorribes, Ivan [1 ]
Yan, Tao [1 ]
Junge, Kathrin [1 ]
Beller, Matthias [1 ]
机构
[1] Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
关键词
homogeneous catalysis; hydrogen; methylation; reduction; ruthenium; HOMOGENEOUS CATALYTIC-HYDROGENATION; IRIDIUM CATALYST; REDUCTION; CO2; METHANOL; TRANSFORMATION; BICARBONATES; DERIVATIVES; ALCOHOLS; AMIDES;
D O I
10.1002/anie.201306850
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Put a label on it: Carbon dioxide with H2 is shown to be an efficient and selective methylation reagent for aromatic and aliphatic amines (see scheme; acac=acetylacetonate, triphos = 1,1,1- tris(diphenylphosphanylmethyl)ethane). A variety of functionalized amines including 13C-labelled drugs were obtained with good yields and functional-group tolerance. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:12156 / 12160
页数:5
相关论文
共 51 条
[1]  
Addis, 2011, ANGEW CHEM, V123, P6128
[2]   Selective Reduction of Carboxylic Acid Derivatives by Catalytic Hydrosilylation [J].
Addis, Daniele ;
Das, Shoubhik ;
Junge, Kathrin ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (27) :6004-6011
[3]  
[Anonymous], 2010, ANGEW CHE, DOI DOI 10.1002/ANGE.201004263
[4]  
[Anonymous], 1995, Angew. Chem., DOI DOI 10.1002/ANGE.19951072005
[5]   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
[6]   Direct Hydrogenation of Amides to Alcohols and Amines under Mild Conditions [J].
Balaraman, Ekambaram ;
Gnanaprakasam, Boopathy ;
Shimon, Linda J. W. ;
Milstein, David .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (47) :16756-16758
[7]  
Beydoun K., 2013, ANGEW CHEM, V125, P9733
[8]   Ruthenium-Catalyzed Direct Methylation of Primary and Secondary Aromatic Amines Using Carbon Dioxide and Molecular Hydrogen [J].
Beydoun, Kassem ;
vom Stein, Thorsten ;
Klankermayer, Juergen ;
Leitner, Walter .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (36) :9554-9557
[9]  
Boddien A., 2011, Angewandte Chemie, V123, P6535, DOI [10.1002/ange.201101995, DOI 10.1002/ANGE.201101995]
[10]   CO2-"Neutral" Hydrogen Storage Based on Bicarbonates and Formates [J].
Boddien, Albert ;
Gaertner, Felix ;
Federsel, Christopher ;
Sponholz, Peter ;
Mellmann, Doerthe ;
Jackstell, Ralf ;
Junge, Henrik ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) :6411-6414