A Mild Chemoselective Ru-Catalyzed Reduction of Alkynes, Ketones, and Nitro Compounds

被引:87
作者
Schabel, Tobias [1 ]
Belger, Christian [1 ]
Plietker, Bernd [1 ]
机构
[1] Univ Stuttgart, Inst Organ Chem, DE-70569 Stuttgart, Germany
关键词
HYDROGEN-TRANSFER REACTIONS; FORMIC-ACID; WATER; NITROARENES; COMPLEXES; OLEFINS; RUTHENIUM; ALDEHYDES; ALKENES; ZINC;
D O I
10.1021/ol401185t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The chemoselective reduction of alkyne, ketones, or nitro groups using (Ph3P)(3)RuCl2 as an inexpensive catalyst and Zn/water as a stoichiometric reductant is reported. Depending on the nature of the additive and the temperature, good chemoselectivities were observed allowing, e.g., for the selective reduction of a nitro group in the presence of a ketone or an alkyne.
引用
收藏
页码:2858 / 2861
页数:4
相关论文
共 28 条
[1]  
Ahluwalia V. K., 2007, GREEN CHEM ENV BENIG
[2]   A highly diastereoselective pinacol coupling reaction of aldehydes and ketones using low-valence niobium generated from Nb(V) [J].
Arai, S ;
Sudo, Y ;
Nishida, A .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2004, 52 (02) :287-288
[3]   Stereoselective Hydrogenation of Aromatic Alkynes Using Water, Triethylsilane, or Methanol, Mediated and Catalyzed by Ni(0) Complexes [J].
Barrios-Francisco, Rigoberto ;
Garcia, Juventino J. .
INORGANIC CHEMISTRY, 2009, 48 (01) :386-393
[4]   A Selective Ru-Catalyzed Semireduction of Alkynes to Z Olefins under Transfer-Hydrogenation Conditions [J].
Belger, Christian ;
Neisius, N. Matthias ;
Plietker, Bernd .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (40) :12214-12220
[5]  
Bigelow HE, 1942, ORG SYNTH, V22, P28
[6]   Unprecedented hydrogen transfer from water to alkenes and alkynes mediated by TiIII and late transition metals [J].
Campana, Araceli G. ;
Estevez, Rosa E. ;
Fuentes, Noelia ;
Robles, Rafael ;
Cuerva, Juan M. ;
Bunuel, Elena ;
Cardenas, Diego ;
Oltra, J. Enrique .
ORGANIC LETTERS, 2007, 9 (11) :2195-2198
[7]   Resolving Heterogeneity Problems and Impurity Artifacts in Operationally Homogeneous Transition Metal Catalysts [J].
Crabtree, Robert H. .
CHEMICAL REVIEWS, 2012, 112 (03) :1536-1554
[8]   Hydrogen transfer from formic acid to alkynes catalyzed by a diruthenium complex [J].
Gao, Y ;
Jennings, MC ;
Puddephatt, RJ .
CANADIAN JOURNAL OF CHEMISTRY, 2001, 79 (5-6) :915-921
[9]  
Imai H., 1976, CHEM LETT, P655
[10]   Efficient and highly selective iron-catalyzed reduction of nitroarenes [J].
Jagadeesh, Rajenahally V. ;
Wienhoefer, Gerrit ;
Westerhaus, Felix A. ;
Surkus, Annette-Enrica ;
Pohl, Marga-Martina ;
Junge, Henrik ;
Junge, Kathrin ;
Beller, Matthias .
CHEMICAL COMMUNICATIONS, 2011, 47 (39) :10972-10974