NNP-Type Pincer Imidazolylphosphine Ruthenium Complexes: Efficient Base-Free Hydrogenation of Aromatic and Aliphatic Nitriles under Mild Conditions

被引:48
作者
Adam, Rosa [1 ]
Alberico, Elisabetta [1 ,2 ]
Baumann, Wolfgang [1 ]
Drexler, Hans-Joachim [1 ]
Jackstell, Ralf [1 ]
Junge, Henrik [1 ]
Beller, Matthias [1 ]
机构
[1] Leibniz Inst Katalyse eV, Albert Einstein Str 29a, D-18059 Rostock, Germany
[2] CNR, Ist Chim Biomol, Tr La Crucca 3, I-07100 Sassari, Italy
关键词
homogeneous catalysis; hydrogenation; N; P ligands; ruthenium; synthesis design; METAL-LIGAND COOPERATION; CARBOXYLIC-ACID ESTERS; CATALYTIC-HYDROGENATION; PRIMARY AMINES; SELECTIVE HYDROGENATION; CARBONYL-COMPOUNDS; CHEMOSELECTIVE HYDROGENATION; COORDINATION CHEMISTRY; BOND ACTIVATION; ALCOHOLS;
D O I
10.1002/chem.201504709
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of seven novel (NNP)-N-Im-P-H-type pincer imidazolylphosphine ruthenium complexes has been synthesized and fully characterized. The use of hydrogenation of benzonitrile as a benchmark test identified [RuHCl(CO)((NNPtBu)-N-Im-P-H)] as the most active catalyst. With its stable Ru-BH4 analogue, in which chloride is replaced by BH4, a broad range of (hetero)aromatic and aliphatic nitriles, including industrially interesting adiponitrile, has been hydrogenated under mild and base-free conditions.
引用
收藏
页码:4991 / 5002
页数:12
相关论文
共 100 条
[1]   Ruthenium N-heterocyclic carbene catalysts for selective reduction of nitriles to primary amines [J].
Addis, Daniele ;
Enthaler, Stephan ;
Junge, Kathrin ;
Wendt, Bianca ;
Beller, Matthias .
TETRAHEDRON LETTERS, 2009, 50 (26) :3654-3656
[2]   Cleavage of unreactive bonds with pincer metal complexes [J].
Albrecht, Martin ;
Lindner, Monika M. .
DALTON TRANSACTIONS, 2011, 40 (35) :8733-8744
[3]   Multidentate actor ligands as versatile platforms for small molecule activation and catalysis [J].
Annibale, Vincent T. ;
Song, Datong .
RSC ADVANCES, 2013, 3 (29) :11432-11449
[4]  
[Anonymous], 2006, ANGEW CHEM, DOI DOI 10.1002/ANGE.200503771
[5]  
[Anonymous], 2012, ANGEW CHEM
[6]  
[Anonymous], 2011, Angew. Chem, DOI DOI 10.1002/ANGE.201105876
[7]   TRANS-INFLUENCE - ITS MEASUREMENT AND SIGNIFICANCE [J].
APPLETON, TG ;
CLARK, HC ;
MANZER, LE .
COORDINATION CHEMISTRY REVIEWS, 1973, 10 (3-4) :335-422
[8]   Recent Advances in Transition Metal-Catalyzed Hydrogenation of Nitriles [J].
Bagal, Dattatraya B. ;
Bhanage, Bhalchandra M. .
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (05) :883-900
[9]   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
[10]   Kinetic evaluation of ligand-hemilability in transition metal complexes [J].
Bassetti, Mauro .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2006, (22) :4473-4482