Synthesis and application of a new polystyrene-supported ruthenium carbene catalyst for alkene metathesis

Nieczypor, Piotr; Buchowicz, Włodzimierz; Meester, Wim J. N.; Rutjes, Floris P. J. T.; Mol, J.C.

doi:10.1016/s0040-4039(01)01460-5

Cited by 98 publications

(63 citation statements)

References 23 publications

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“…Merrifield resins functionalized with hydroxyethyl groups are first reacted with perfluoroglutaric anhydride, and the carboxylic acid thus formed is converted into the corresponding silver salt, which upon reaction with [Cl 2 RuA C H T U N G T R E N N U N G (=CHPh)-A C H T U N G T R E N N U N G (PCy 3 ) 2 ] provides an immobilized Grubbs I catalyst (10a). [44] In a similar way, using the hydroxymethylfunctionalized Merrifield resins, the immobilized Grubbs II catalyst can be prepared (10b). [45] A Grubbs II catalyst can also be supported on monoliths (10c) or silica (10d).…”

Section: Immobilization By Exchanging Chloride Ligandsmentioning

confidence: 99%

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

Copéret,

Basset

2007

Adv Synth Catal

213

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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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Section: Immobilization By Exchanging Chloride Ligandsmentioning

confidence: 99%

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

Copéret,

Basset

2007

Adv Synth Catal

213

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“…Filtration at the end of the reaction allows an easy separation of the product and recovery of the catalyst, avoiding time-consuming chromatography. Anchoring of ruthenium alkylidenes of type 1 and 2 to the polymeric matrix has been performed via phosphine exchange, [6] via the N-heterocyclic carbene ligand, [7] through halogen exchange, [8] or via alkylidene exchange (boomerang-type catalysts).…”

Section: Introductionmentioning

confidence: 99%

Hybrid Organic‐Inorganic Materials Derived from a Monosilylated Hoveyda‐type Ligand as Recyclable Diene and Enyne Metathesis Catalysts

et al. 2007

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The synthesis of a monosilylated Hoveydatype monomer is described as well as the preparation of several organic-inorganic hybrid materials derived from it by sol-gel processes and by anchoring to commercial silica gel and MCM-41. The resulting materials were treated with first and/or second generation Grubbs catalyst to generate HoveydaGrubbs type alkylidene ruthenium complexes covalently bonded to the silica matrix. These materials are efficient recyclable catalysts for the ring-closing metathesis reaction of dienes and enynes, even for the formation of tri-and tetrasubstituted olefins.

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“…Mol and co-workers exchanged one of the chloride ligands on Grubbs precatalyst and bound this catalyst to a Merrifield-type resin with a perfluorinated linker. [43] The resulting heterogenized complex 21 (Table 2, entry 1) showed reduced reactivity compared to the homogeneous parent analogue and displayed substantial loss of activity after the second run. This should not necessarily be ascribed to a lack of tight attachment of the organometallic fragment to the support but rather reflects the inherent low stability of 2 type precatalysts that also translates into appreciable amounts of Ru contamination in the metathesis product.…”

Section: Immobilization Through Anionic Ligands Xmentioning

confidence: 99%

“…Catalyst 35, [55] covalently immobilized on silica, exhibited a lower activity in RCM than its homogeneous counterpart; nevertheless, it could be reused up to three times. 1 [43] 6 (23 %) 156 2 [47] n.d. [c] 0.083 3 [47] n.d.…”

Section: N-heterocyclic Carbenesmentioning

confidence: 99%

Sustainable Concepts in Olefin Metathesis

et al. 2007

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Ruthenium-catalyzed olefin metathesis reactions represent an attractive and powerful transformation for the formation of new carbon-carbon double bonds. This area is now quite familiar to most chemists as numerous catalysts are available that enable a plethora of olefin metathesis reactions. Nevertheless, with the exception of uses in polymerization reactions, only a limited number of industrial processes use olefin metathesis. This is mainly due to difficulties associated with removing ruthenium from the final products. In this context, a number of studies have been carried out to develop procedures for the removal of the catalyst or the products of catalyst decomposition, however, none are universally attractive so far. This situation has resulted in tremendous activity in the area dealing with supported or tagged versions of homogeneous catalysts. This Review summarizes the numerous studies focused on developing cleaner ruthenium-catalyzed metathesis processes.

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Synthesis and application of a new polystyrene-supported ruthenium carbene catalyst for alkene metathesis

Cited by 98 publications

References 23 publications

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

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

Hybrid Organic‐Inorganic Materials Derived from a Monosilylated Hoveyda‐type Ligand as Recyclable Diene and Enyne Metathesis Catalysts

Sustainable Concepts in Olefin Metathesis

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