On water and in air: Fast and highly chemoselective transfer hydrogenation of aldehydes with iridium catalysts

被引:191
作者
Wu, Xiaofeng [1 ]
Liu, Jianke [1 ]
Li, Xiaohong [1 ]
Zanotti-Gerosa, Antonio [1 ]
Hancock, Fred [1 ]
Vinci, Daniele [1 ]
Ruan, Jiwu [1 ]
Xiao, Jianliang [1 ]
机构
[1] Univ Liverpool, Dept Chem, Liverpool Ctr Mat & Catalysis, Liverpool L69 7ZD, Merseyside, England
关键词
aldehydes; chemoselectivity; iridium; transfer hydrogenation; water;
D O I
10.1002/anie.200602122
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Water as solvent: A fast, selective, and high-yielding transfer hydrogenation of a wide range of aldehydes is achieved using IrIII catalysts containing simple ethylene-diamine (en) ligands (see scheme; Ts = p-toluenesulfonyl, TOF = turnover frequency). This procedure is suitable for aldehydes with a wide range of functional groups. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6718 / 6722
页数:5
相关论文
共 36 条
[1]   Isolation and crystal structure of a water-soluble iridium hydride: A robust and highly active catalyst for acid-catalyzed transfer hydrogenations of carbonyl compounds in acidic media [J].
Abura, T ;
Ogo, S ;
Watanabe, Y ;
Fukuzumi, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (14) :4149-4154
[2]   The biphasic transfer hydrogenation of aldehydes and ketones with isopropanol catalyzed by water-soluble rhodium complexes [J].
Ajjou, AN ;
Pinet, JL .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 214 (02) :203-206
[3]  
[Anonymous], 2004, ANGEW CHEM, V43, P6731, DOI DOI 10.1002/ANGE.200460102
[4]  
Blacker J., 2004, ASYMMETRIC CATALYSIS, P201, DOI DOI 10.1002/3527602151.CH11
[5]   Water-soluble arene ruthenium complexes containing a trans-1,2-diaminocyclohexane ligand as enantioselective transfer hydrogenation catalysts in aqueous solution [J].
Canivet, J ;
Labat, G ;
Stoeckli-Evans, H ;
Süss-Fink, G .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2005, (22) :4493-4500
[6]  
CARNIVET J, 2005, J ORGANOMET CHEM, V690, P3209
[7]   New developments in hydrogenation catalysis particularly in synthesis of fine and intermediate chemicals [J].
Chen, B ;
Dingerdissen, U ;
Krauter, JGE ;
Rotgerink, HGJL ;
Möbus, K ;
Ostgard, DJ ;
Panster, P ;
Riermeier, TH ;
Seebald, S ;
Tacke, T ;
Trauthwein, H .
APPLIED CATALYSIS A-GENERAL, 2005, 280 (01) :17-46
[8]   Mechanisms of the H2-hydrogenation and transfer hydrogenation of polar bonds catalyzed by ruthenium hydride complexes [J].
Clapham, SE ;
Hadzovic, A ;
Morris, RH .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2201-2237
[9]   Asymmetric transfer hydrogenation: chiral ligands and applications [J].
Gladiali, S ;
Alberico, E .
CHEMICAL SOCIETY REVIEWS, 2006, 35 (03) :226-236
[10]   Bifunctional transition metal-based molecular catalysts for asymmetric syntheses [J].
Ikariya, T ;
Murata, K ;
Noyori, R .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (03) :393-406