Diruthenium complex catalyzed reduction of nitroarenes-investigation of reaction pathway

被引:19
作者
Lin, Shih-Chieh Aaron [1 ]
Liu, Yi-Hung [1 ]
Peng, Shie-Ming [1 ]
Liu, Shiuh-Tzung [1 ]
机构
[1] Natl Taiwan Univ, Dept Chem, Taipei, Taiwan
关键词
Diruthenium; Reduction; Nitroarene; Hydrazine; Aniline; AROMATIC NITRO-COMPOUNDS; TRANSFER HYDROGENATION; NITROBENZENE; CONVENIENT;
D O I
10.1016/j.mcat.2019.01.005
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
A diruthenium complex, [(L)Ru-2(eta(6)-C6H6)(2)Cl-2](PF6)(2) (1) (L = 5-phenyl-2,8-di-2-pyridinylanthyridine), was prepared and characterized. This diruthenium complex 1 was found to be an efficient catalyst for the reduction of aromatic nitro compounds leading to the corresponding aniline derivatives with the use of hydrazine as the reducing agent at 80 degrees C in an ethanol solution. Catalytic activity of 1 towards various possible intermediates leading to anilines was investigated to understand the reaction pathway. These studies indicate that this reduction proceeds via a direct route as evidenced by hydroxylamines being observed as the major intermediate followed by the appearance of aniline under the catalytic conditions. Thus, the reaction pathway of this catalytic system is discussed.
引用
收藏
页码:46 / 51
页数:6
相关论文
共 24 条
[1]   Nitrosobenzene as a hydrogen acceptor in rhodium catalysed dehydrogenation reactions of alcohols: synthesis of aldehydes and azoxybenzenes [J].
Annen, Samuel P. ;
Gruetzmacher, Hansjoerg .
DALTON TRANSACTIONS, 2012, 41 (46) :14137-14145
[2]  
[Anonymous], 2015, Acta Crystallogr., V71, P3
[3]  
[Anonymous], 2001, The Nitro Group in Organic Synthesis
[4]   A Review on Bimetallic Nickel-Based Catalysts for CO2 Reforming of Methane [J].
Bian, Zhoufeng ;
Das, Sonali ;
Wai, Ming Hui ;
Hongmanorom, Plaifa ;
Kawi, Sibudjing .
CHEMPHYSCHEM, 2017, 18 (22) :3117-3134
[5]   Iridium-catalyzed transfer hydrogenation of nitroarenes to anilines [J].
Chen, Shujie ;
Lu, Guoping ;
Cai, Chun .
NEW JOURNAL OF CHEMISTRY, 2015, 39 (07) :5360-5365
[6]   A different reaction pathway for the reduction of aromatic nitro compounds on gold catalysts [J].
Corma, Avelino ;
Concepcion, Patricia ;
Serna, Pedro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (38) :7266-7269
[7]   Convenient synthesis of tris-heteroleptic ruthenium(II) polypyridyl complexes [J].
Freedman, DA ;
Evju, JK ;
Pomije, MK ;
Mann, KR .
INORGANIC CHEMISTRY, 2001, 40 (22) :5711-+
[8]   Cooperative bimetallic catalysis in asymmetric allylic substitution [J].
Fu, Jingke ;
Huo, Xiaohong ;
Li, Bowen ;
Zhang, Wanbin .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (46) :9747-9759
[9]   The hydrogenation of nitrobenzene to aniline: a new mechanism [J].
Gelder, EA ;
Jackson, SD ;
Lok, CM .
CHEMICAL COMMUNICATIONS, 2005, (04) :522-524
[10]   Catalytic activation of hydrazine hydrate by gold nanoparticles: Chemoselective reduction of nitro compounds into amines [J].
Gkizis, Petros L. ;
Stratakis, Manolis ;
Lykakis, Ioannis N. .
CATALYSIS COMMUNICATIONS, 2013, 36 :48-51