Ionic-liquid-supported synthesis: A novel liquid-phase strategy for organic synthesis

被引:435
作者
Miao, Weishi [1 ]
Chan, Tak Hang
机构
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China
关键词
D O I
10.1021/ar030252f
中图分类号
O6 [化学];
学科分类号
0703 [化学];
摘要
Soluble ionic liquids have recently been used as supports for catalyst/reagent immobilization and synthesis in homogeneous solution phase. The wide range of ionic liquid supports available makes their use as supports compatible with most common chemistries. The solubility properties of these ionic liquid supports can be tuned by the variation of cations and anions to make them phase separate from less polar organic solvents and aqueous media. The ionic-liquid-supported species can therefore be purified from the reaction mixture by simple washings. Ionic-liquid-supported catalysts and reagents have been prepared and used, and they are easily recovered and reused. Parallel and combinatorial libraries of small molecules have been synthesized. Ionic-liquid-supported synthesis (ILSS) has been applied to the preparation of oligopeptides and oligosaccharides. The comparison of ILSS with solid-phase synthesis, soluble-polymer-supported synthesis, and fluorous phase synthesis has been highlighted where applicable.
引用
收藏
页码:897 / 908
页数:12
相关论文
共 56 条
[1]
Synthesis and preliminary use of novel acrylic ester-derived task-specific ionic liquids [J].
Anjaiah, S ;
Chandrasekhar, S ;
Grée, R .
TETRAHEDRON LETTERS, 2004, 45 (03) :569-571
[2]
An ionic liquid-supported ruthenium carbene complex: A robust and recyclable catalyst for ring-closing olefin metathesis in ionic liquids [J].
Audic, N ;
Clavier, H ;
Mauduit, M ;
Guillemin, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (31) :9248-9249
[3]
Chiral vanadyl salen complex anchored on supports as recoverable catalysts for the enantioselective cyanosilylation of aldehydes.: Comparison among silica, single wall carbon nanotube, activated carbon and imidazolium ion as support [J].
Baleizao, C ;
Gigante, B ;
García, H ;
Corma, A .
TETRAHEDRON, 2004, 60 (46) :10461-10468
[4]
CO2 capture by a task-specific ionic liquid [J].
Bates, ED ;
Mayton, RD ;
Ntai, I ;
Davis, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (06) :926-927
[5]
LIQUID-PHASE SYNTHESIS OF PEPTIDES [J].
BAYER, E ;
MUTTER, M .
NATURE, 1972, 237 (5357) :512-&
[6]
Benaglia M, 2002, ADV SYNTH CATAL, V344, P533, DOI 10.1002/1615-4169(200207)344:5<533::AID-ADSC533>3.0.CO
[7]
2-Y
[8]
Using soluble polymers to recover catalysts and ligands [J].
Bergbreiter, DE .
CHEMICAL REVIEWS, 2002, 102 (10) :3345-3383
[9]
HELP (HIGH-EFFICIENCY LIQUID-PHASE) NEW OLIGONUCLEOTIDE SYNTHESIS ON SOLUBLE POLYMERIC SUPPORT [J].
BONORA, GM ;
SCREMIN, CL ;
COLONNA, FP ;
GARBESI, A .
NUCLEIC ACIDS RESEARCH, 1990, 18 (11) :3155-3159
[10]
BROWN RCD, 1998, J CHEM SOC P1, V1, P3293