ROMP-Spheres:  A Novel High-Loading Polymer Support Using Cross Metathesis between Vinyl Polystyrene and Norbornene Derivatives

Barrett, Anthony G. M.; Cramp, Susan M.; Roberts, Richard S.

doi:10.1021/ol9908878

Cited by 93 publications

(38 citation statements)

References 19 publications

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“…[ Olefin Cross-Metathesis Angewandte Chemie "ROMP-spheres" have distinct swelling properties, and functional diversity of the polymers is possible simply by varying the norbornene moiety. [124] Cuny and co-workers have applied solid-phase ROM-CM of bicyclic alkenes with styrene derivatives to combinatorial library synthesis using resin-bound norbornenes. [125] In an interesting application, substituted norbornenes were subjected to ROM-CM conditions in the presence of substituted styrenes, followed by acid-induced cleavage from the resin with concurrent formation of a cyclopentene-fused piperidinone ring (Scheme 35).…”

Section: Reactions On a Solid Supportmentioning

confidence: 99%

Recent Developments in Olefin Cross‐Metathesis

2003

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Among the many types of transition-metal-catalyzed C-C bond-forming reactions, olefin metathesis has come to the fore in recent years owing to the wide range of transformations that are possible with commercially available and easily handled catalysts. Consequently, olefin metathesis is now widely considered as one of the most powerful synthetic tools in organic chemistry. Until recently the intermolecular variant of this reaction, cross-metathesis, had been neglected despite its potential. With the evolution of new catalysts, the selectivity, efficiency, and functional-group compatibility of this reaction have improved to a level that was unimaginable just a few years ago. These advances, together with a better understanding of the mechanism and catalyst-substrate interactions, have brought us to a stage where more and more researchers are employing cross-metathesis reactions in multistep procedures and in the synthesis of natural products. The recent inclusion of alkynes and hindered bicyclic olefins as viable substrates for bimolecular metathesis coupling, the discovery of enantioselective cross-metathesis and cross-metathesis in water, and the successful marriage of metathesis and solid-phase organic synthesis has further widened the scope of this versatile reaction.

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Section: Reactions On a Solid Supportmentioning

confidence: 99%

Recent Developments in Olefin Cross‐Metathesis

2003

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“…However, the contamination of the final product by Ru is decreased using these catalysts. Additionally, these systems can be used to prepared polymer beads with high loading of functionalities, [56] stationary phase of liquid chromatography, [57][58][59] ] or star-polymers based on simple first-generation dendrimers [60,61] through ROMP.…”

Section: The Grubbs I and Ii Catalystsmentioning

confidence: 99%

Strategies to Immobilize Well‐Defined Olefin Metathesis Catalysts: Supported Homogeneous Catalysis vs. Surface Organometallic Chemistry

Copéret,

Basset

2007

Adv Synth Catal

210

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This review is mainly devoted to a description of the strategies that have been implemented to develop well-defined olefin metathesis catalysts immobilized on solid supports. Two main approaches have been investigated involving supported homogenous catalysts or heterogeneous catalysts prepared by surface organometallic chemistry. Advantages, limitations and possible developments of these systems are discussed.

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“…Seit unseren ersten Arbeiten [11,12] Barrett et al [124] beschrieben die Immobilisierung von ROMP-Norbornen-Polymeren an Vinylpolystyrol durch ROM-CM. Die so erhaltenen "ROMP-Kugeln" haben charakteristische Quelleigenschaften, und durch Wahl der Norborneneinheit kann eine Diversität in der Funktionalität des Polymers einfach hergestellt werden.…”

Section: Kreuzmetathesen Am Festen Trägerunclassified

Jüngste Entwicklungen bei der gekreuzten Olefinmetathese

2003

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Unter den vielen übergangsmetallvermittelten C‐C‐verknüpfenden Reaktionen ist die Olefinmetathese in den letzten Jahren durch die große Bandbreite an möglichen Umsetzungen mit käuflichen und leicht handhabbaren Katalysatoren hervorgetreten und gilt heutzutage als eine der mächtigsten Synthesemethoden in der Organischen Chemie. Die intermolekulare Variante dieser Reaktion, die Kreuzmetathese, führte trotz ihres hohen synthetischen Nutzens bis vor kurzem eher ein Schattendasein. Durch die Entwicklung neuer, besserer Katalysatoren konnte die Selektivität, die Toleranz gegen funktionelle Gruppen und die Effizienz der Katalyse jedoch auf ein Niveau gesteigert werden, das noch bis vor wenigen Jahren als unvorstellbar galt. Dank dieser Fortschritte und dem verbesserten Verständnis des Reaktionsmechanismus und der Katalysator‐Substrat‐Wechselwirkungen werden Kreuzmetathesen heute in zunehmendem Maße in mehrstufigen Reaktionssequenzen und Naturstoffsynthesen verwendet. Die kürzlich vorgestellte Einbeziehung von Alkinen und sterisch gehinderten bicyclischen Olefinen als Substrate für bimolekulare Kupplungen, die Entwicklung von enantioselektiven und in Wasser ausführbaren Kreuzmetathesen und die erfolgreiche Kombination der Olefinmetathese und der Festphasensynthese in der Organischen Chemie haben die Anwendungsbreite der Kreuzmetathese noch zusätzlich vergrößert.

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ROMP-Spheres: A Novel High-Loading Polymer Support Using Cross Metathesis between Vinyl Polystyrene and Norbornene Derivatives

Cited by 93 publications

References 19 publications

Recent Developments in Olefin Cross‐Metathesis

Recent Developments in Olefin Cross‐Metathesis

Strategies to Immobilize Well‐Defined Olefin Metathesis Catalysts: Supported Homogeneous Catalysis vs. Surface Organometallic Chemistry

Jüngste Entwicklungen bei der gekreuzten Olefinmetathese

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