Organic reactions in low melting mixtures based on carbohydrates and L-carnitine-a comparison

被引:149
作者
Ilgen, Florian [1 ]
Koenig, Burkhard [1 ]
机构
[1] Univ Regensburg, Inst Organ Chem, D-93040 Regensburg, Germany
关键词
UREA-SALT MIXTURES; IONIC LIQUIDS; REGIOSELECTIVE SYNTHESIS; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; 1,3-DIPOLAR CYCLOADDITION; SUPERCRITICAL FLUIDS; GREEN SOLVENTS; HECK REACTION; CATALYST; PALLADIUM;
D O I
10.1039/b816551c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new L-carnitine/urea melt was developed and compared to previously reported sugar and sugar alcohol melts using several organic reactions for benchmarking. Physicochemical properties of the new L-carnitine melt, including the melting point and the polarity were determined by differential scanning calorimetry (DSC) and solvatochromatic measurements, respectively. The L-carnitine melt shows a very high polarity. Heck and Sonogashira cross-couplings, Diels-Alder reactions and Cu-catalysed 1,3-dipolar cycloadditions proceed cleanly in sugar and L-carnitine based melts, but the applicability of L-carnitine melts for standard organic reactions is limited by their lower thermal stability.
引用
收藏
页码:848 / 854
页数:7
相关论文
共 68 条
[1]  
ALFONSO C, 2005, GREEN SEPARATION PRO
[2]  
Alvarez SG, 1997, SYNTHESIS-STUTTGART, P413
[3]  
Anastas P., 1998, GREEN CHEM THEORY PR
[4]  
[Anonymous], 1984, 1 3 DIPOLAR CYCLOADD
[5]   A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction [J].
Appukkuttan, P ;
Dehaen, W ;
Fokin, VV ;
Van der Eycken, E .
ORGANIC LETTERS, 2004, 6 (23) :4223-4225
[6]  
BASTIDE J, 1973, B SOC CHIM FR
[7]   CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].
Bock, VD ;
Hiemstra, H ;
van Maarseveen, JH .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68
[8]   A highly active and reusable copper(I)-tren catalyst for the "click'' 1,3-dipolar cycloaddition of azides and alkynes [J].
Candelon, Nicolas ;
Lastecoueres, Dominique ;
Diallo, Abdou Khadri ;
Aranzaes, Jaime Ruiz ;
Astruc, Didier ;
Vincent, Jean-Marc .
CHEMICAL COMMUNICATIONS, 2008, (06) :741-743
[9]   The Heck reaction in ionic liquids: A multiphasic catalyst system [J].
Carmichael, AJ ;
Earle, MJ ;
Holbrey, JD ;
McCormac, PB ;
Seddon, KR .
ORGANIC LETTERS, 1999, 1 (07) :997-1000
[10]   Polytriazoles as copper(I)-stabilizing ligands in catalysis [J].
Chan, TR ;
Hilgraf, R ;
Sharpless, KB ;
Fokin, VV .
ORGANIC LETTERS, 2004, 6 (17) :2853-2855