A recyclable ‘boomerang’ polymer-supported ruthenium catalyst for olefin metathesis

Ahmed, Mahmood; Barrett, Anthony G. M.; Braddock, D. Christopher; Cramp, Susan M.; Procopiou, Panayiotis A.

doi:10.1016/s0040-4039(99)01833-x

Cited by 181 publications

(81 citation statements)

References 15 publications

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“…[133] Although active and recyclable in metathesis reactions, this catalyst was considerably slower than its homogeneous analogue. Barrett and co-workers [134,135] devised a general CM-based immobilization strategy whereby the reaction between vinyl polystyrene (PS) and either 3 or 6 generates catalysts 152 or 153, respectively. These catalysts (used at 2.5-5 mol % levels) were reasonably active in RCM reactions and could be recycled several times.…”

Section: Of Polymer-supported Catalystsmentioning

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: Of Polymer-supported Catalystsmentioning

confidence: 99%

Recent Developments in Olefin Cross‐Metathesis

2003

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“…This can be achieved by reaction of Grubbs I [50][51][52][53] or Grubbs II [54,55] catalysts with a macroporous polystyrene or poly-DVB resin having pendant vinyl groups. In these heterogeneous catalysts, the active species is in fact a homogeneous catalyst, and it is not clear how much of Ru is then re-incorporated as the initial carbene (boomerang concept), because of a significant loss of activity after each cycle.…”

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

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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“…Barrett and coworkers 60,61 heterogenized bisphosphane ruthenium complex 1 on polystyrene and evidenced that it was possible to use the supported catalyst in RCM of ethyl diallylmalonate and ROMP of norbornene. Highly efficient immobilized catalysts have been obtained from NHC ruthenium alkylidene complexes deposited on various solid supports.…”

Section: G1 60mentioning

confidence: 99%

Recent developments in design and synthesis of well-defined ruthenium metathesis catalysts – a highly successful opening for intricate organic synthesis

Drăguţan¹,

Drăguţan²,

Filip³

2005

Arkivoc

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Dedicated to Professor Alexandru T. Balaban on the occasion of his AbstractThis paper surveys the latest and fast growing developments in the design and synthesis of homogeneous and immobilized ruthenium metathesis catalysts. These novel ruthenium carbene complexes, devised as convenient counterparts of the well-defined tungsten and molybdenum alkylidene complexes, display comparable activity and selectivity in metathesis reactions combined with good tolerance towards organic functionalities, air and moisture. Due to their valuable attributes, they have been applied successfully in a multitude of complex organic and polymer syntheses involving ring-opening and ring-closing metathesis reactions, crossmetathesis, enyne metathesis and ring-opening metathesis polymerization.

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A recyclable ‘boomerang’ polymer-supported ruthenium catalyst for olefin metathesis

Cited by 181 publications

References 15 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

Recent developments in design and synthesis of well-defined ruthenium metathesis catalysts – a highly successful opening for intricate organic synthesis

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