Pushing Back the Limits of Hydrosilylation: Unprecedented Catalytic Reduction of Organic Ureas to Formamidines

被引:30
作者
Pouessel, Jacky [1 ]
Jacquet, Olivier [1 ]
Cantat, Thibault [1 ]
机构
[1] CEA, IRAMIS, CNRS, SIS2M,UMR 3299, F-91191 Gif Sur Yvette, France
关键词
hydrosilylation; iron; reduction; silanes; ureas; N-HETEROCYCLIC CARBENE; CARBON-DIOXIDE; CARBOXYLIC-ACIDS; SELECTIVE REDUCTION; SUBSTITUTED UREAS; CHEMOSELECTIVE REDUCTION; SECONDARY AMIDES; AROMATIC-AMINES; METAL-COMPLEXES; CO2;
D O I
10.1002/cctc.201300653
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Pushing back the limits: A novel catalytic transformation has been designed to prepare formamidine derivatives by reduction of substituted ureas with hydrosilanes. Simple iron catalysts based on commercially available iron salts and phosphine ligands prove to be highly active in promoting this new hydrosilylation reaction. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:3552 / 3556
页数:5
相关论文
共 83 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]   Green chemistry tools to influence a medicinal chemistry and research chemistry based organisation [J].
Alfonsi, Kim ;
Colberg, Juan ;
Dunn, Peter J. ;
Fevig, Thomas ;
Jennings, Sandra ;
Johnson, Timothy A. ;
Kleine, H. Peter ;
Knight, Craig ;
Nagy, Mark A. ;
Perry, David A. ;
Stefaniak, Mark .
GREEN CHEMISTRY, 2008, 10 (01) :31-36
[4]  
Anderson P. G, 2008, MODERN REDUCTION MET
[5]  
[Anonymous], 2012, ANGEW CHEM
[6]  
[Anonymous], 2010, ANGEW CHE, DOI DOI 10.1002/ANGE.201004263
[7]   Unprecedented Catalytic Hydrogenation of Urea Derivatives to Amines and Methanol [J].
Balaraman, Ekambaram ;
Ben-David, Yehoshoa ;
Milstein, David .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (49) :11702-11705
[8]  
Balaraman E, 2011, NAT CHEM, V3, P609, DOI [10.1038/NCHEM.1089, 10.1038/nchem.1089]
[9]   N,N'-BRIDGED 1,4,5,8-TETRAKIS(METHYLAMINO)NAPHTHALENES AND THEIR RADICAL CATIONS - COMPARISON WITH 1,4,5,8-TETRAKIS(DIMETHYLAMINO)NAPHTHALENE AND RELATED RADICAL CATIONS [J].
BARTH, T ;
NEUGEBAUER, FA .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) :5401-5406
[10]  
Bates H. A., 1986, J ORG CHEM, V51, p228