Microwave-Assisted Olefin Metathesis

[en] Since the first reports on the use of microwave irradiation to accelerate organic chemical transformations, a plethora of papers have been published in this field. In most examples, microwave heating has been shown to dramatically reduce reaction times, increase product yields, and enhance product purity by reducing unwanted side reactions compared to conventional heating methods. The present contribution aims at illustrating the advantages of this technology in olefin metathesis and, when data are available, at comparing microwave-heated and conventionally heated experiments.

Disciplines :

Chemistry

Author, co-author :

Nicks, François

Borguet, Yannick ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Sauvage, Xavier

Bicchielli, Dario ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Delfosse, Sébastien

Delaude, Lionel ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Demonceau, Albert ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Language :

English

Title :

Microwave-Assisted Olefin Metathesis

Publication date :

2010

Main work title :

Green Metathesis Chemistry

Editor :

Dragutan, Valerian

Demonceau, Albert ; Université de Liège - ULiège > Département de chimie (sciences)

Dragutan, Ileana

Finkelshtein, Eugene Sh.

Publisher :

Springer, Dordrecht, Netherlands

ISBN/EAN :

978-90-481-3431-1

Collection name :

NATO Science for Peace and Security Series A: Chemistry and Biology

Pages :

327-358

Available on ORBi :

since 27 April 2010

Statistics

Number of views

121 (12 by ULiège)

Number of downloads

2 (1 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

OpenAlex citations

Bibliography

For some recent monographs on microwave-assisted reactions, see: (a) Hayes BL (2002) Microwave synthesis: chemistry at the speed of light, 1st edn., CEM, Matthews, NC;
(b) Microwaves in organic and medicinal chemistry. In Kappe CO, Stadler A (eds.) (2005) Methods and principles in medicinal chemistry, vol. 25, Wiley-VCH, Weinheim, Germany;
(c) Loupy A (2006) Microwaves in organic synthesis, 2nd edn., Wiley-VCH, Weinheim, Germany
For some recent reviews on microwave-assisted reactions, see: (a) Perreux L, Loupy A (2001) A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations. Tetrahedron 57: 9199-9223;
(b) Lidström P, Tierney J, Wathey B, Westman J (2001) Microwave-assisted organic synthesis - a review. Tetrahedron 57: 9225-9283;
(c) Larhed M, Moberg C, Hallberg A (2002) Microwaveaccelerated homogeneous catalysis in organic chemistry. Acc Chem Res 35: 717-717;
(d) Kappe CO (2004) Controlled microwave heating in modern organic synthesis. Angew Chem Int Ed 43: 6250-6284;
(e) Hayes BL (2004) Recent advances in microwave-assisted synthesis. Aldrichim Acta 37: 66-76;
(f) Nüchter M, Ondruschka B, Bonrath W, Gum A (2004) Microwave-assisted synthesis - a critical technology overview. Green Chem 6: 128-141;
(g) Xu Y, Guo QX. (2004) Syntheses of heterocyclic compounds under microwave irradiation. Heterocycles 63: 903-974;
(h) Desai B, Kappe CO (2004) Microwave-assisted synthesis involving immobilized catalysts. Top Curr Chem 242: 177-208;
(i) de la Hoz A, Diaz-Ortiz A, Moreno A (2005) Activation of organic reactions by microwaves. Adv Org Synth 1: 119-171;
(j) Dallinger D, Kappe CO (2007) Microwave-assisted synthesis in water as solvent. Chem Rev 107: 2563-2591;
(k) Baxendale IR, Hayward JJ, Ley SV (2007) Microwave reactions under continuous flow conditions. Comb Chem High Throughput Screen 10: 802-836;
(l) Kappe CO (2008) Microwave dielectric heating in synthetic organic chemistry. Chem Soc Rev 37: 1127-1139;
(m) Polshettiwar V, Varma RS (2008) Aqueous microwave chemistry: a clean and green synthetic tool for rapid drug discovery. Chem Soc Rev 37: 1546-1557;
(n) Appukkuttan P, Van der Eycken E (2008) Recent developments in microwave-assisted, transition-metal-catalysed C-C and C-N bond-forming reactions. Eur J Org Chem 1133-1155
Varray S, Gauzy C, Lamaty F, Lazaro R, Martinez J (2000) Synthesis of cyclic amino acid derivatives via ring closing metathesis on a poly(ethylene glycol) supported substrate. J Org Chem 65: 6787-6790
Coquerel Y, Rodriguez J (2008) Microwave-assisted olefin metathesis. Eur J Org Chem 1125-1132
(a) Geng X, Danishefsky SJ (2004) Total synthesis of aigialomycin D. Org Lett 6: 413-416;
(b) Yang ZQ, Geng X, Solit D, Pratilas CA, Rosen N, Danishefsky SJ (2004) New efficient synthesis of resorcinylic macrolides via ynolides: establishment of cycloproparadicicol as synthetically feasible preclinical anticancer agent based on Hsp90 as the target. J Am Chem Soc 126: 7881-7889
Vu NQ, Chai CLL, Lim KP, Chia SC, Chen A (2007) An efficient and practical total synthesis of aigialomycin D. Tetrahedron 63: 7053-7058
Nosse B, Schall A, Jeong WB, Reiser O (2005) Optimization of ring-closing metathesis: inert gas sparging and microwave irradiation. Adv Synth Catal 347: 1869-1874
Benakki H, Colacino E, André C, Guenoun F, Martinez J, Lamaty F (2008) Microwave-assisted multi-step synthesis of novel pyrrolo-[3,2-c]quinoline derivatives. Tetrahedron 64: 5949-5955
Declerck V, Ribière P, Martinez J, Lamaty F (2004) Sequential aza-Baylis-Hillman/ring closing metathesis/aromatization as a novel route for the synthesis of substituted pyrroles. J Org Chem 69: 8372-8381
(a) O'Brien CJ, Kantchev EAB, Valente C, Hadei N, Chass GA, Lough A, Hopkinson AC, Organ MG (2006) Easily prepared air- and moisture-stable Pd-NHC (NHC = N-heterocyclic carbene) complexes: a reliable, user-friendly, highly active palladium precatalyst for the Suzuki-Miyaura reaction. Chem Eur J 12: 4743-4748;
(b) Organ MG, Avola S, Dubovyk I, Hadei N, Kantchev EAB, O'Brien CJ, Valente C (2006) A user-friendly, all-purpose Pd-NHC (NHC = N-heterocyclic carbene) precatalyst for the Negishi reaction: a step towards a universal cross-coupling catalyst. Chem Eur J 12: 4749-4755
Lamberto M, Kilburn JD (2008) Synthesis of indolizidines from dialkylated isocyanides: a novel radical cyclisation/N-alkylation/ring closing metathesis approach. Tetrahedron Lett 49: 6364-6367
Jam F, Tullberg M, Luthman K, Grøtli M (2007) Microwave assisted synthesis of spiro-2,5-diketopiperazines. Tetrahedron 63: 9881-9889
Hammer K, Undheim K (1997) Ruthenium(II) in ring closing metathesis for the stereoselective preparation of cyclic 1-amino-1-carboxylic acids. Tetrahedron 53: 2309-2322
Terracciano S, Bruno I, D'Amico E, Bifulco G, Zampella A, Sepe V, Smith CD, Riccio R (2008) Synthetic and pharmacological studies on new simplified analogues of the potent actin-targeting jaspamide. Bioorg Med Chem 16: 6580-6588
Robinson AJ, Elaridi J, van Lierop BJ, Mujcinovic S, Jackson WR (2007) Microwave-assisted RCM for the synthesis of carbocyclic peptides. J Pept Sci 13: 280-285
See also: (a) Robinson AJ, Garland R, Illesinghe J, van Lierop B, Gooding S, Whelan A, Elaridi J, Teoh E, Jackson WR, Applying homogeneous catalysis to the synthesis of peptidomimetics, 16th International Symposium on Homogeneous Catalysis, Florence (Italy), July 6-11, 2008, abstract P 373;
(b) Illesinghe J, Garland R, Xing Guo C, Ahmed A, van Lierop B, Jackson WR, Robinson AJ, Metathesis-assisted synthesis of cyclic peptides, 16th International Symposium on Homogeneous Catalysis, Florence (Italy), July 6-11, 2008, abstract P 374
Elaridi J, Patel J, Jackson WR, Robinson AJ (2006) Controlled synthesis of (S,S)-2,7-diaminosuberic acid: a method for regioselective construction of dicarba analogues of multicystine-containing peptides. J Org Chem 71: 7538-7545
See also: Teoh E, Garland R, Illesinghe J, Whelan A, Kozowski Z, Jackson WR, Robinson AJ, Using cross metathesis to generate peptide-polymer hybrids, 16th International Symposium on Homogeneous Catalysis, Florence (Italy), July 6-11, 2008, abstract P 375
Lumini M, Cordero FM, Pisaneschi F, Brandi A (2008) Straightforward synthesis of α-substituted prolines by cross-metathesis. Eur J Org Chem 2817-2824
Goldup SM, Pilkington CJ, White AJP, Burton A, Barrett AGM (2006) A simple, short, and flexible synthesis of viridiofungin derivatives. J Org Chem 71: 6185-6191
Lombardo M, Capdevila MG, Pasi F, Trombini C (2006) An efficient high-yield synthesis of D-ribo-phytosphingosine. Org Lett 8: 3303-3305
Hayashi Y, Regnier T, Nishiguchi S, Sydnes MO, Hashimoto D, Hasegawa J, Katoh T, Kajimoto T, Shiozuka M, Matsuda R, Node M, Kiso Y (2008) Efficient total synthesis of (+)-negamycin, a potential chemotherapeutic agent for genetic diseases. Chem Commun 2379-2381
Gebauer J, Arseniyadis S, Cossy J (2008) Total synthesis of cystothiazole A by microwaveassisted olefin cross-metathesis. Eur J Org Chem 2701-2704
Jackson R, Gartshore C, Illesinghe J, Robinson AJ, A metathesis route to spirocyclic alkaloid precursors, 16th International Symposium on Homogeneous Catalysis, Florence (Italy), July 6-11, 2008, abstract P 378
Artman GD III, Grubbs AW, Williams RM (2007) Concise, asymmetric, stereocontrolled total synthesis of stephacidins A, B and notoamide B. J Am Chem Soc 129: 6336-6342
Debleds O, Campagne JM (2008) 1,5-Enyne metathesis. J Am Chem Soc 130: 1562-1563
Nicolaou KC, Brenzovich WE, Bulger PG, Francis TM (2006) Synthesis of iso-epoxyamphidinolide N and des-epoxy-carabenolide I structures. Initial forays. Org Biomol Chem 4: 2119-2157
(a) Castagnolo D, Renzulli ML, Galletti E, Corelli F, Botta M (2005) Microwave-assisted ethylene-alkyne cross-metathesis: synthesis of chiral 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes. Tetrahedron: Asymmetry 16: 2893-2896;
(b) Castagnolo D, Giorgi G, Spinosa R, Corelli F, Botta M (2007) Practical syntheses of enantiomerically pure Nacetylbenzhydrylamines. Eur J Org Chem 3676-3686
Mortreux A, Blanchard M (1974) Metathesis of alkynes by a molybdenum hexacarbonyl-resorcinol catalyst. J Chem Soc Chem Commun 786-787
Villemin D, Héroux M, Blot V (2001) Silanol-molybdenum hexacarbonyl as a new efficient catalyst for metathesis of functionalised alkynes under microwave irradiation. Tetrahedron Lett 42: 3701-3703
Fürstner A, Stelzer F, Rumbo A, Krause H (2002) Total synthesis of the turrianes and evaluation of their DNA-cleaving properties. Chem Eur J 8: 1856-1871
Efskind J, Undheim K (2003) High temperature microwave-accelerated rutheniumcatalysed domino RCM reactions. Tetrahedron Lett 44: 2837-2839
Dhanalakshmi K, Sundararajan G (1997) Microwave-assisted polymerisation of phenylacetylenes. Polym Bull 39: 333-337
Jhaveri SB, Carter KR (2007) Disubstituted polyacetylene brushes grown via surfacedirected tungsten-catalyzed polymerization. Langmuir 23: 8288-8290
de la Hoz A, Diaz-Ortiz Á, Moreno A (2005) Microwaves in organic synthesis. Thermal and non-thermal microwave effects. Chem Soc Rev 34: 164-178
Garbacia S, Desai B, Lavastre O, Kappe CO (2003) Microwave-assisted ring-closing metathesis revisited. On the question of the nonthermal microwave effect. J Org Chem 68: 9136-9139
Herrero MA, Kremsner JM, Kappe CO (2008) Nonthermal microwave effects revisited: on the importance of internal temperature monitoring and agitation in microwave chemistry. J Org Chem 73: 36-47
Gilday JP, Lenden P, Moseley JD, Cox BG (2008) The Newman-Kwart rearrangement: a microwave kinetic study. J Org Chem 73: 3130-3134
Teske JA, Deiters A (2008) Microwave-mediated nickel-catalyzed cyclo-trimerization reactions: total synthesis of illudine. J Org Chem 73: 342-345
Razzaq T, Kappe CO (2008) On the energy efficiency of microwave-assisted organic reactions. ChemSusChem 1: 123-132