Comprehensive study on olefin metathesis in PEG as an alternative solvent under microwave irradiation

被引:34
作者
Bantreil, Xavier [1 ]
Sidi-Ykhlef, Mohammed [1 ]
Aringhieri, Laura [1 ]
Colacino, Evelina [1 ]
Martinez, Jean [1 ]
Lamaty, Frederic [1 ]
机构
[1] Univ Montpellier 2, Inst Biomols Max Mousseron, UMR CNRS UM I UM II 5247, F-34095 Montpellier 5, France
关键词
Metathesis; Polyethylene glycol; Microwave-assisted synthesis; Isomerization; Hydride; Ruthenium; RING-CLOSING METATHESIS; N-HETEROCYCLIC CARBENE; POLY(ETHYLENE GLYCOL); RUTHENIUM CARBENE; PRIMARY ALCOHOLS; CATALYSTS; COMPLEXES; EFFICIENT; DESIGN; ISOMERIZATION;
D O I
10.1016/j.jcat.2012.07.007
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070305 [高分子化学与物理];
摘要
Polyethylene glycols (PEGs) are non-toxic, biodegradable and sustainable organic solvents, which find a large application in the chemical and pharmaceutical industry. In this study, we present the ring-closing metathesis reaction (RCM) in PEG under microwave irradiation. Several benchmark substrates, yielding 5- to 6-membered rings featuring di- or tri-substituted olefins, were evaluated. This study demonstrated that PEGs are suitable solvent for olefin metathesis. However, depending on the substrate/catalyst couple, isomerization may occur. (C) 2012 Elsevier Inc. All rights reserved.
引用
收藏
页码:113 / 118
页数:6
相关论文
共 53 条
[1]
Arlt D., 2008, PCT Int. Appl., Patent No. [WO2008034552, 2008034552]
[2]
Bailey Jr F.E, 1976, POLYETHYLENE OXIDE
[3]
Ring-closing metathesis in glycerol under microwave activation [J].
Bakhrou, Naoual ;
Lamaty, Frederic ;
Martinez, Jean ;
Colacino, Evelina .
TETRAHEDRON LETTERS, 2010, 51 (30) :3935-3937
[4]
Mixed N-heterocyclic carbene/phosphite ruthenium complexes: towards a new generation of olefin metathesis catalysts [J].
Bantreil, Xavier ;
Schmid, Thibault E. ;
Randall, Rebecca A. M. ;
Slawin, Alexandra M. Z. ;
Cazin, Catherine S. J. .
CHEMICAL COMMUNICATIONS, 2010, 46 (38) :7115-7117
[5]
Rational Design and Evaluation of Upgraded Grubbs/Hoveyda Olefin Metathesis Catalysts: Polyfunctional Benzylidene Ethers on the Test Bench [J].
Bieniek, Michal ;
Samojlowicz, Cezary ;
Sashuk, Volodymyr ;
Bujok, Robert ;
Sledz, Pawel ;
Lugan, Noel ;
Lavigne, Guy ;
Arlt, Dieter ;
Grela, Karol .
ORGANOMETALLICS, 2011, 30 (15) :4144-4158
[6]
In an attempt to provide a user's guide to the galaxy of benzylidene, alkoxybenzylidene, and indenylidene ruthenium olefin metathesis catalysts [J].
Bieniek, Micho ;
Michrowska, Anna ;
Usanov, Dmitry L. ;
Grela, Karol .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (03) :806-818
[7]
Polyethylene glycol and solutions of polyethylene glycol as green reaction media [J].
Chen, J ;
Spear, SK ;
Huddleston, JG ;
Rogers, RD .
GREEN CHEMISTRY, 2005, 7 (02) :64-82
[8]
Cu(I)-Catalyzed Intramolecular C-C Coupling of Activated Methylene Compounds with Vinyl Halides: Efficient Synthesis of Functionalized Alkylidenecyclobutanes [J].
Chen, Liqun ;
Shi, Min ;
Li, Chaozhong .
ORGANIC LETTERS, 2008, 10 (22) :5285-5288
[9]
N-heterocyclic carbene and phosphine ruthenium indenylidene precatalysts: A comparative study in Olefin metathesis [J].
Clavier, Herve ;
Nolan, Steven P. .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (28) :8029-8036
[10]
A pyridine-containing ruthenium-indenylidene complex: Synthesis and activity in ring-closing metathesis [J].
Clavier, Herve ;
Petersen, Jeffrey L. ;
Nolan, Steven P. .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (24-25) :5444-5447