Olefin metathesis in room temperature ionic liquids using imidazolium-tagged ruthenium complexes

被引:103
作者
Clavier, H [1 ]
Audic, N [1 ]
Guillemin, JC [1 ]
Mauduit, M [1 ]
机构
[1] Ecole Natl Super Chim Rennes, Inst CHim Rennes, Lab Synth & Activat Biomol, CNRS,UMR 6052, F-35700 Rennes, France
关键词
supported catalysts; olefin metathesis; ionic liquid;
D O I
10.1016/j.jorganchem.2005.04.009
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
New recyclable imidazolium-tagged ruthenium catalysts have been developed to perform olefin metathesis in room temperature ionic liquids (RTILs). High level of recyclability combined with a high reactivity were obtained in the ring-closing metathesis (RCM) of a variety of di- or tri-substituted and/or oxygen-containing dienes. Extremely low residual ruthenium levels were detected in the RCM products (average of 7.3 ppm per run). Several examples of olefin cross-metathesis (CM) have been also studied. (c) 2005 Elsevier B.V. All rights reserved.
引用
收藏
页码:3585 / 3599
页数:15
相关论文
共 55 条
[1]   Ruthenium carbene complexes with imidazolin-2-ylidene ligands allow the formation of tetrasubstituted cycloalkenes by RCM [J].
Ackermann, L ;
Fürstner, A ;
Weskamp, T ;
Kohl, FJ ;
Herrmann, WA .
TETRAHEDRON LETTERS, 1999, 40 (26) :4787-4790
[2]   A recyclable 'boomerang' polymer-supported ruthenium catalyst for olefin metathesis [J].
Ahmed, M ;
Barrett, AGM ;
Braddock, DC ;
Cramp, SM ;
Procopiou, PA .
TETRAHEDRON LETTERS, 1999, 40 (49) :8657-8662
[3]   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
[4]   Recovery of organic products from ionic liquids using supercritical carbon dioxide [J].
Blanchard, LA ;
Brennecke, JF .
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2001, 40 (01) :287-292
[5]  
BLECHERT S, 2003, INT ED ENGL, V42, P1900
[6]   Recent advances in the synthesis of supported metathesis catalysts [J].
Buchmeiser, MR .
NEW JOURNAL OF CHEMISTRY, 2004, 28 (05) :549-557
[7]   Ruthenium-catalyzed olefin metathesis in ionic liquids [J].
Buijsman, RC ;
van Vuuren, E ;
Sterrenburg, JG .
ORGANIC LETTERS, 2001, 3 (23) :3785-3787
[8]  
CHAUVIN Y, 1976, MAKROMOL CHEM, V177, P2637
[9]  
CHAUVIN Y, 1973, C R SEANCES ACAD S C, V276, P169
[10]   An efficient method for removal of ruthenium byproducts from olefin metathesis reactions [J].
Cho, JH ;
Kim, BM .
ORGANIC LETTERS, 2003, 5 (04) :531-533