Easy Ruthenium-Catalysed Oxidation of Primary Amines to Nitriles under Oxidant-Free Conditions

被引:30
作者
Achard, Thierry [1 ]
Egly, Julien [1 ]
Sigrist, Michel [1 ]
Maisse-Francois, Aline [1 ]
Bellemin-Laponnaz, Stephane [1 ]
机构
[1] Univ Strasbourg, Dept Mat Organ, IPCMS, CNRS UMR 7504, 23 Rue Loess,BP 43, F-67034 Strasbourg 2, France
关键词
acceptorless dehydrogenation; dehydrogenation; homogenous catalysis; nitrile; ruthenium; DEHYDROGENATION; COMPLEXES; CONVERSION;
D O I
10.1002/chem.201902557
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A dehydrogenation of primary amine to give the corresponding nitrile under oxidant- and base-free conditions catalysed by simple [Ru(p-cym)Cl-2](2) with no extra ligand is reported. The system is highly selective for alkyl amines, whereas benzylamine derivatives gave the nitrile product together with the imine in a ratio ranging from 14:1 to 4:1 depending on the substrate. Preliminary mechanistic investigations have been performed to identify the key factors that govern the selectivity.
引用
收藏
页码:13271 / 13274
页数:4
相关论文
共 43 条
[1]   The catalytic activity of a cyclometalated ruthenium(III) complex for aerobic oxidative dehydrogenation of benzylamines [J].
Aiki, Shota ;
Taketoshi, Ayako ;
Kuwabara, Junpei ;
Koizumi, Take-aki ;
Kanbara, Takaki .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (06) :1301-1304
[2]   Preparation of imine complexes of ruthenium and osmium stabilised by [MCl(η6-p-cymene)(PR3)]+ fragments [J].
Albertin, Gabriele ;
Antoniutti, Stefano ;
Castro, Jesus .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2010, 695 (04) :574-579
[3]  
[Anonymous], [No title captured]
[4]  
[Anonymous], 2012, ANGEW CHEM
[5]   Transition metal-catalyzed dehydrogenation of amines [J].
Broere, Daniel L. J. .
PHYSICAL SCIENCES REVIEWS, 2018, 3 (09)
[6]   Atom-economic dehydrogenative amide synthesis via ruthenium catalysis [J].
Chen, Cheng ;
Verpoort, Francis ;
Wu, Qiongyou .
RSC ADVANCES, 2016, 6 (60) :55599-55607
[7]   Mechanisms of imine exchange reactions in organic solvents [J].
Ciaccia, Maria ;
Di Stefano, Stefano .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (03) :646-654
[8]   Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis [J].
Corma, Avelino ;
Navas, Javier ;
Sabater, Maria J. .
CHEMICAL REVIEWS, 2018, 118 (04) :1410-1459
[9]   Homogeneous Transition Metal Catalysis of Acceptorless Dehydrogenative Alcohol Oxidation: Applications in Hydrogen Storage and to Heterocycle Synthesis [J].
Crabtree, Robert H. .
CHEMICAL REVIEWS, 2017, 117 (13) :9228-9246
[10]   Resolving Heterogeneity Problems and Impurity Artifacts in Operationally Homogeneous Transition Metal Catalysts [J].
Crabtree, Robert H. .
CHEMICAL REVIEWS, 2012, 112 (03) :1536-1554