Metal-containing ionic liquids as efficient catalysts for hydroxymethylation in water

被引:64
作者
Bica, Katharina [1 ]
Gaertner, Peter [1 ]
机构
[1] Vienna Univ Technol, Inst Appl Synthet Chem, A-1060 Vienna, Austria
关键词
ionic liquids; iron; water chemistry; hydroxymethylation; lactones;
D O I
10.1002/ejoc.200800323
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The iron-containing ionic liquid butylmethylimidazolium tetrachloroferrate (bmim-FeCl4) proved to be an efficient and recyclable catalyst for the hydroxymethylation of beta-keto esters using aqueous formaldehyde and a low catalyst loading of up to 0.1 mol-% without co-solvents or additional surfactants. An useful and high-yielding approach to hydroxymethylated keto esters as well as to 3-disubstitued butyrolactones via tandem hydroxymethylation-lactonization could thus be established. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
引用
收藏
页码:3453 / 3456
页数:4
相关论文
共 30 条
[11]  
Guzaev A, 1997, SYNTHESIS-STUTTGART, P1281
[12]   Discovery of a magnetic ionic liquid [bmim]FeCl4 [J].
Hayashi, S ;
Hamaguchi, HO .
CHEMISTRY LETTERS, 2004, 33 (12) :1590-1591
[13]  
KUWANO H, 2005, NUCLEOS NUCLEOT NUCL, V24, P73
[14]   Iron(III)-catalyzed tandem sequential methanol oxidation/aldol coupling [J].
Lecomte, V ;
Bolm, C .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1666-1672
[15]  
LONGERAY R, 1964, B SOC CHIM FR, P2849
[16]   Synthesis of 5-aryl-2-oxopyrrole derivatives as synthons for highly substituted pyrroles [J].
Metten, Bert ;
Kostermans, Maarten ;
Van Baelen, Gitte ;
Smet, Mario ;
Dehaen, Wim .
TETRAHEDRON, 2006, 62 (25) :6018-6028
[17]   Iron-catalyzed direct-type hydroxymethylation of 1,3-dicarbonyl compounds in water [J].
Ogawa, Chikako ;
Kobayashi, Shu .
CHEMISTRY LETTERS, 2007, 36 (01) :56-57
[18]   Current progress in the asymmetric aldol addition reaction [J].
Palomo, C ;
Oiarbide, M ;
García, JM .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (02) :65-75
[19]   Catalysis in ionic liquids [J].
Parvulescu, Vasile I. ;
Hardacre, Christopher .
CHEMICAL REVIEWS, 2007, 107 (06) :2615-2665
[20]   THE FREE RADICAL ADDITION OF ALDEHYDES TO UNSATURATED POLYCARBOXYLIC ESTERS [J].
PATRICK, TM .
JOURNAL OF ORGANIC CHEMISTRY, 1952, 17 (07) :1009-1016