The Development of L<sub>2</sub>X<sub>2</sub>RuCHR Olefin Metathesis Catalysts:  An Organometallic Success Story

Trnka, Tina M.; Grubbs, Robert H.

doi:10.1021/ar000114f

Cited by 3,508 publications

(1,702 citation statements)

References 96 publications

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“…When these polymerizations have fast initiation and slow propagation rates, polymers of narrow polydispersity can be generated. [150] Such polymerization reactions can be used to synthesize multivalent ligands with a variety of sizes. For example, linear polymers with molecular weights of approximately 3,000 generated via ring-opening metathesis polymerization (ROMP) can span 100 nm.…”

Section: 3dmentioning

confidence: 99%

“…[101,149,[154][155][156][157][158] Ruthenium carbene catalysts for ROMP can be used to generate materials of distinct valency. [150,[159][160][161] These ligands have been generated as inhibitors of saccharide-protein interactions, [151,[162][163][164] as ligands for combating vancomycin-resistant bacteria, [156] and as effectors of biological responses. [46,165] Importantly, this polymerization method allows control over the RE display and density.…”

Section: 3dmentioning

confidence: 99%

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Synthetic Multivalent Ligands as Probes of Signal Transduction

2006

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Cell surface receptors acquire information from the extracellular environment and coordinate intracellular responses. Evidence from biochemical and structural studies indicates that many receptors do not operate as individual entities, but rather as part of higher-order complexes (e.g. dimers and oligomers). Coupling the functions of multiple receptors may endow signaling pathways with the sensitivity and malleability required to govern cellular responses. Moreover, multireceptor signaling complexes may provide a means of spatially segregating otherwise degenerate signaling cascades. Despite the proposed importance of receptor-receptor processes in cellular signaling, questions concerning the mechanisms, extent, and consequences of receptor co-localization and interreceptor communication remain unanswered.Chemical synthesis can provide a variety of compounds with which to address the role of receptor assembly in signal transduction. The focus of this review is one such approach -the use of synthetic multivalent ligands to characterize receptor function. Multivalent ligands can be generated that possess a variety of sizes, shapes, valencies, orientations, and densities of binding elements. Their unique architectures imbue multivalent ligands with the ability to access binding modes not available to monovalent compounds. Multivalent ligands, therefore, are capable of illuminating aspects of inter-receptor processes that are not readily probed using conventional approaches. We suggest that, as focus shifts from investigations of the function of individual proteins and toward the analysis of multi-receptor signaling complexes, multivalent ligands will become even more valuable tools with which to ask sophisticated mechanistic questions. Further, multivalent ligands may provide new opportunities for manipulating receptor systems for the deconvolution of pathways, diagnosis, and, ultimately, the treatment of disease.

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Section: 3dmentioning

confidence: 99%

Section: 3dmentioning

confidence: 99%

Synthetic Multivalent Ligands as Probes of Signal Transduction

2006

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“…Eventually, the loss of ethylene from the metal coordination sphere results in entropic driving force to give the cross alkene metathesis product. A full summary of Grubbs' mechanistic work [45][46][47] and a selectivity model for alkene metathesis [48] are available. The methylidene plays a critical role in alkene metathesis by linking catalytic cycles.…”

Section: Mechanism: An Introductionmentioning

confidence: 99%

Ruthenium vinyl carbene intermediates in enyne metathesis

Diver

2007

Coordination Chemistry Reviews

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This review provides an overview of ruthenium vinyl carbene reactivity as it relates to enyne metathesis. Methods for the synthesis of metathesis-active and metathesis-inactive complexes are also summarized. Some of the early hypotheses about vinyl carbene intermediates in enyne metatheses were tested in the arena of synthetic chemistry and subsequently led to mechanistic studies. In these two areas, studies from the author's labs are described. There are still many unresolved questions in enyne metathesis that trace back to vinyl carbene reactivity. Hopefully this review will stimulate further investigation into vinyl carbene reactivity which should further refine our understanding of catalytic enyne metathesis.

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“…These catalysts are exceptionally tolerant of air, moisture, and a wide variety of functional groups. [2] This has enabled their widespread use in numerous applications. Recent studies using ruthenium-based olefin metathesis catalysts have succeeded at developing Z-selective ruthenium catalysts.…”

Section: Stereoretentive Metathesis Using Rutheniummentioning

confidence: 99%

“…Olefin metathesis has become an indispensable method for the formation of carbon-carbon double bonds, [1][2][3][4][5] finding use in synthetic organic, [6][7][8] biological, [9][10][11] and materials chemistry. [12][13][14] The ubiquity of olefin metathesis as a synthetic tool has been linked to the evolution of catalysts from ill-defined mixtures to well-characterized molecular species based on molybdenum, ruthenium and tungsten.…”

Section: Introductionmentioning

confidence: 99%

Stereoretentive Olefin Metathesis: An Avenue to Kinetic Selectivity

2017

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Abstract:Olefin metathesis is an incredibly valuable transformation that has gained widespread use in both academic and industrial settings. Lately, stereoretentive olefin metathesis has garnered much attention as a method for the selective generation of both Eand Z-olefins. Early studies employing ill-defined catalysts showed evidence for retention of the starting olefins at early conversion. However, thermodynamic ratios were reached as the reaction proceeded to equilibrium. Recent studies in olefin metathesis have focused on the synthesis of catalysts that can overcome the inherent thermodynamic preference of an olefin, providing synthetically useful quantities of a kinetically favored olefin isomer. These reports have led to the development of stereoretentive catalysts that not only generate Z-olefins selectively, but also kinetically produce E-olefins, a previously unmet challenge in olefin metathesis. Advancements in stereoretentive olefin metathesis using tungsten, ruthenium, and molybdenum catalysts are presented.

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The Development of L₂X₂RuCHR Olefin Metathesis Catalysts: An Organometallic Success Story

Cited by 3,508 publications

References 96 publications

Synthetic Multivalent Ligands as Probes of Signal Transduction

Synthetic Multivalent Ligands as Probes of Signal Transduction

Ruthenium vinyl carbene intermediates in enyne metathesis

Stereoretentive Olefin Metathesis: An Avenue to Kinetic Selectivity

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The Development of L2X2RuCHR Olefin Metathesis Catalysts: An Organometallic Success Story

Cited by 3,508 publications

References 96 publications

Synthetic Multivalent Ligands as Probes of Signal Transduction

Synthetic Multivalent Ligands as Probes of Signal Transduction

Ruthenium vinyl carbene intermediates in enyne metathesis

Stereoretentive Olefin Metathesis: An Avenue to Kinetic Selectivity

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Product

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The Development of L₂X₂RuCHR Olefin Metathesis Catalysts: An Organometallic Success Story