Mild palladium-catalysed highly efficient hydrogenation of CN, C-NO2, and C=O bonds using H2 of 1 atm in H2O

被引:38
作者
Liu, Yaxu [1 ]
He, Shaopo [1 ]
Quan, Ziyi [1 ]
Cai, Huizhuo [1 ]
Zhao, Yang [1 ]
Wang, Bo [1 ,2 ,3 ]
机构
[1] Hainan Univ, Key Lab Adv Mat Trop Isl Resources, Minist Educ, 58 Renmin Ave, Haikou 570228, Hainan, Peoples R China
[2] Hainan Univ, State Key Lab Marine Resource Utilizat South Chin, 58 Renmin Ave, Haikou 570228, Hainan, Peoples R China
[3] Hainan Univ, Inst Chem Engn, Coll Mat & Chem Engn, 58 Renmin Ave, Haikou 570228, Hainan, Peoples R China
基金
国家重点研发计划; 中国国家自然科学基金;
关键词
PRIMARY AMINES; SELECTIVE HYDROGENATION; NITRILE HYDROGENATION; COBALT CATALYSTS; NANOPARTICLES; REDUCTION; AMINATION; DEHYDROGENATION; COMPLEXES; ALDEHYDES;
D O I
10.1039/c8gc03285h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Here we present the first example of a mild and high-efficiency protocol enabling a process in water using 1 atm of H-2 for the efficient and selective hydrogenation of nitriles, nitro compounds, ketones, and aldehydes to yield primary amines and alcohols with satisfactory yields of up to >99%. Several palladium-based nanoparticle catalysts were prepared from K2PdCl4 and ligands, and one of them was found to be the best and most suitable for the hydrogenation of C?N, C-NO2, and C?O bonds. In addition, the catalyst Pd-NPs can be easily recycled and reused without losing their activity and selectivity. A plausible mechanism for the hydrogenation of a C?N bond was also proposed, representing the first example that possesses great potential for sustainable industrial purposes.
引用
收藏
页码:830 / 838
页数:9
相关论文
共 47 条
[1]   NNP-Type Pincer Imidazolylphosphine Ruthenium Complexes: Efficient Base-Free Hydrogenation of Aromatic and Aliphatic Nitriles under Mild Conditions [J].
Adam, Rosa ;
Alberico, Elisabetta ;
Baumann, Wolfgang ;
Drexler, Hans-Joachim ;
Jackstell, Ralf ;
Junge, Henrik ;
Beller, Matthias .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (14) :4991-5002
[2]   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
[3]   Utilization of Common Ligands for the Ruthenium-Catalyzed Amination of Alcohols [J].
Baumann, Wolfgang ;
Spannenberg, Anke ;
Pfeffer, Jan ;
Haas, Thomas ;
Koeckritz, Angela ;
Martin, Andreas ;
Deutsch, Jens .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (52) :17702-17706
[4]   Mild and selective hydrogenation of aromatic and aliphatic (di) nitriles with a well-defined iron pincer complex [J].
Bornschein, Christoph ;
Werkmeister, Svenja ;
Wendt, Bianca ;
Jiao, Haijun ;
Alberico, Elisabetta ;
Baumann, Wolfgang ;
Junge, Henrik ;
Junge, Kathrin ;
Beller, Matthias .
NATURE COMMUNICATIONS, 2014, 5
[5]   Selective hydrogenation of nitriles to primary amines catalyzed by a novel iron complex [J].
Chakraborty, Subrata ;
Leitus, Gregory ;
Milstein, David .
CHEMICAL COMMUNICATIONS, 2016, 52 (09) :1812-1815
[6]   Stable and Inert Cobalt Catalysts for Highly Selective and Practical Hydrogenation of CN and C=O Bonds [J].
Chen, Feng ;
Topf, Christoph ;
Radnik, Joerg ;
Kreyenschulte, Carsten ;
Lund, Henrik ;
Schneider, Matthias ;
Surkus, Annette-Enrica ;
He, Lin ;
Junge, Kathrin ;
Beller, Matthias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (28) :8781-8788
[7]   Two Iron Catalysts are Better than One: A General and Convenient Reduction of Aromatic and Aliphatic Primary Amides [J].
Das, Shoubhik ;
Wendt, Bianca ;
Moeller, Konstanze ;
Junge, Kathrin ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (07) :1662-1666
[8]   Selective Catalytic Hydrogenations of Nitriles, Ketones, and Aldehydes by Well-Defined Manganese Pincer Complexes [J].
Elangovan, Saravanakumar ;
Topf, Christoph ;
Fischer, Steffen ;
Jiao, Haijun ;
Spannenberg, Anke ;
Baumann, Wolfgang ;
Ludwig, Ralf ;
Junge, Kathrin ;
Beller, Matthias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (28) :8809-8814
[9]   A General and Environmentally Benign Catalytic Reduction of Nitriles to Primary Amines [J].
Enthaler, Stephan ;
Addis, Daniele ;
Junge, Kathrin ;
Erre, Giulia ;
Beller, Matthias .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (31) :9491-9494
[10]   General and Highly Efficient Iron-Catalyzed Hydrogenation of Aldehydes, Ketones, and ,α,β-Unsaturated Aldehydes [J].
Fleischer, Steffen ;
Zhou, Shaolin ;
Junge, Kathrin ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (19) :5120-5124