Methylation of secondary amines with dialkyl carbonates and hydrosilanes catalysed by iron complexes

被引：59
作者：
Zheng, Jianxia [1 ]
Darcel, Christophe [1 ]
Sortais, Jean-Baptiste [1 ]
机构：
[1] Univ Rennes 1, UMR CNRS 6226, Inst Sci Chim Rennes, Team Organometall Mat & Catalysis, F-35042 Rennes, France
来源：
CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 91期
关键词：
DIMETHYL CARBONATE; EFFICIENT HYDROSILYLATION; REDUCTIVE AMINATION; MOLECULAR-HYDROGEN; CARBOXYLIC-ACIDS; DIOXIDE; NITRILES; ESTERIFICATION; SELECTIVITY; ALDEHYDES;
D O I：
10.1039/c4cc05517a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Methylation of secondary amines was achieved using dimethyl carbonate or diethyl carbonate as the C-1 source under the catalysis of well-defined half-sandwich iron complexes bearing an N-heterocyclic carbene ligand. The reaction proceeded under mild conditions in the presence of hydrosilanes as the reductants, and the amines were obtained with good to excellent isolated yields.
引用
收藏
页码：14229 / 14232
页数：4
相关论文
共 38 条
[1]   Dimethylcarbonate: a modern green reagent and solvent [J].
Arico, F. ;
Tundo, P. .
RUSSIAN CHEMICAL REVIEWS, 2010, 79 (06) :479-489
[2]   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
[3]   Iron-Catalyzed Hydrosilylation of Esters [J].
Bezier, David ;
Venkanna, Gopaladasu T. ;
Castro, Luis C. Misal ;
Zheng, Jianxia ;
Roisnel, Thierry ;
Sortais, Jean-Baptiste ;
Darcel, Christophe .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (10) :1879-1884
[4]   Cyclopentadienyl-NHC Iron Complexes for Solvent-Free Catalytic Hydrosilylation of Aldehydes and Ketones [J].
Bezier, David ;
Jiang, Fan ;
Roisnel, Thierry ;
Sortais, Jean-Baptiste ;
Darcel, Christophe .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2012, (09) :1333-1337
[5]   Well-Defined Cyclopentadienyl NHC Iron Complex as the Catalyst for Efficient Hydrosilylation of Amides to Amines and Nitriles [J].
Bezier, David ;
Venkanna, Gopaladasu T. ;
Sortais, Jean-Baptiste ;
Darcel, Christophe .
CHEMCATCHEM, 2011, 3 (11) :1747-1750
[6]   Upgrading of Levulinic Acid with Dimethylcarbonate as Solvent/Reagent [J].
Caretto, Alessio ;
Perosa, Alvise .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (08) :989-994
[7]   NHC-carbene cyclopentadienyl iron based catalyst for a general and efficient hydrosilylation of imines [J].
Castro, Luis C. Misal ;
Sortais, Jean-Baptiste ;
Darcel, Christophe .
CHEMICAL COMMUNICATIONS, 2012, 48 (01) :151-153
[8]  
Clarke H. T., 1933, J AM CHEM SOC, V55, P4571, DOI [DOI 10.1021/JA01338A041, 10.1021/ja01338a041]
[9]   Methylation of amines, nitrobenzenes and aromatic nitriles with carbon dioxide and molecular hydrogen [J].
Cui, Xinjiang ;
Dai, Xingchao ;
Zhang, Yan ;
Deng, Youquan ;
Shi, Feng .
CHEMICAL SCIENCE, 2014, 5 (02) :649-655
[10]   Layered Double Hydroxide-Supported L-Methionine-Catalyzed Chemoselective O-Methylation of Phenols and Esterification of Carboxylic Acids with Dimethyl Carbonate: A "Green" Protocol [J].
Dhakshinamoorthy, Amarajothi ;
Sharmila, Alagarsamy ;
Pitchumani, Kasi .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (04) :1128-1132
1234