[en] Olefin metathesis is a metal-catalysed organic reaction, which involves the statistical redistribution of carbon-carbon double bonds. Since its discovery in the 1950's, this transformation has gained widespread use in research laboratories and industry for making products ranging, from drugs and polymers to enhanced fuels. Its advantages include the ability to build up complex structural scaffolds with remarkable atom economy. Major industrial processes usually rely on inexpensive, ill-defined, multicomponent catalytic systems, while research laboratory applications take advantage of well-defined metal alkylidene complexes of molybdenum and ruthenium that combine high activities and ease of set-up under reproducible conditions, albeit at the price of a higher cost.
Disciplines :
Chemistry
Author, co-author :
Demonceau, Albert ; Université de Liège - ULiège > Chimie macromoléculaire et catalyse organique
Delaude, Lionel ; Université de Liège - ULiège > Chimie macromoléculaire et catalyse organique
Language :
English
Title :
Olefin metathesis reactions state of the art and outlook
K. J. Ivin, J. C. Mol, "Olefin Metathesis and Metathesis Polymerization", Academic Press, London (1997);
A. M. Rouhi, Chem. Eng. News December 23, pp. 29-33 (2002);
R. H. Grubbs Ed., Handbook of Metathesis, Wiley-VCH, Weinheim (2003);
D. Astruc, New J. Chem. 29, pp. 42-56 (2005);
D. Astruc, New J. Chem. 30, pp. 1848-1852 (2006);
L Delaude, A. F. Noels, "Metathesis" in: Kirk-Othmer Encyclopedia of Chemical Technology, 5th Print Ed., Vol. 26, A. Seidel Ed.; Wiley, New York, pp. 920-958 (2007).
R. L. Banks, CHEMTECH 16, pp. 112-117 (1986);
H. S. Eleuterio, J. Mol. Catal. 65, pp. 55-61 (1991).
N. Calderon, Acc. Chem. Res. 5, pp. 127-132 (1972).
For a survey of earlier proposals, see: A. M. Rouhi, Chem. Eng. News, December 23, pp. 34-38 (2002).
J.-L. Hérisson, Y. Chauvin, Makromol. Chem. 141, pp. 161-176 (1971).
R. R. Schrock, A. H. Hoveyda, Angew. Chem. Int. Ed. 42, pp. 4592-4633 (2003);
R. R. Schrock, Chem. Commun., pp. 2773-2777 (2005).
S. T. Nguyen, L. K. Johnson et al., J. Am. Chem. Soc. 114, pp. 3974-3975 (1992).
T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 34, pp. 18-29 (2001);
R. H. Grubbs, Tetrahedron 60, pp. 7117-7140 (2004).
W. A. Herrmann, C. Köcher, Angew. Chem. Int. Ed. Engl. 36, pp. 2162-2187 (1997);
W. A. Herrmann, T. Weskamp et al., Adv. Organomet. Chem. 48, pp. 1-69 (2001);
W. A. Herrmann, Angew. Chem. Int. Ed. Engl. 41, pp. 1290-1309 (2002).
Y. Schrodi, R. L. Perderson, Aldrichimica Acta 40, pp. 45-52 (2007).
A. H. Hoveyda, D. G. Gillingham et al., Org. Biomol. Chem. 2, pp. 8-23 (2004).
T. W. Funk, J. M. Berlin et al., J. Am. Chem. Soc. 128, pp. 1840-1846 (2006).
J. C. Mol, Green Chem. 4, pp. 5-13 (2002);
J. C. Mol, J. Mol. Catal. A: Chem. 213, pp. 39-45 (2004);
M. Yamazaki, J. Mol. Catal. A: Chem. 213, pp. 81-87 (2004).
M. Schuster, S. Blechert, Angew. Chem. Int. Ed. Engl. 36, pp.2036-2056 (1997);
S. J. Connon, S. Blechert, Angew. Chem. Int. Ed. Engl. 42, pp. 1900-1923 (2003);
R. L. Pederson, I. M. Fellows et al., Adv. Synth. Catal. 6-7, pp. 728-735 (2002).
M. R. Buchmeiser, Chem. Rev. 100, pp. 1565-1604 (2000);
U. Frenzel, O. Nuyken, J. Polym. Sci. A: Polym. Chem. 40, pp. 2895-2916 (2002);
C. Slugovc, Macromol. Rapid Commun. 25, pp. 1283-1297 (2004).
A. M. Thayer, Chem. Eng. News, February 12, pp. 37-47 (2007).
T. Nicola, M. Brenner et al., Org. Process Res. Dev. 9, pp. 513-515 (2005);
Y. S. Tsantrizos, J.-M. M. Ferland et al., J. Organomet. Chem. 691, pp. 5163-5171 (2006);
N. K. Yee, V. Farina et al., J. Org. Chem. 71, pp. 7133-7145 (2006).
Y. Chauvin, Angew. Chem. Int. Ed. 45, pp. 3741-3747 (2006);
R. R. Schrock, Angew. Chem. Int. Ed. 45, pp. 3748-3759 (2006);
R. H. Grubbs, Angew. Chem. Int. Ed. 45, pp. 3760-3765 (2006).