Ligand Exchange Strategy for Delivery of Ruthenium Complex Unit to Biomolecules Based on Ruthenium–Olefin Specific Interactions

Jatmika, Catur; Wakabayashi, Kazumo; Tamaki, Ryosei; Akiyama, Naoki; Nakamura, Ibuki; Hirota, Shun; Yamaguchi, Hiroyasu; Matsuo, Takashi

doi:10.1246/cl.200590

Cited by 4 publications

(1 citation statement)

References 21 publications

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“…We chose a Hoveyda–Grubbs second-generation ruthenium complex ( H2 ) in which the active site is encompassed by bulky mesityl rings. Because of the danger of poisoning the metal center with the sulfur of thiol group, the precatalyst was generated in situ in the reaction between the styrene moieties of the adsorbed SAT ligands and a commercial Grubbs second-generation ruthenium complex ( G2 ). The reaction was performed in the presence of copper(I) chloride to shift the equilibrium toward the product by catching the releasing phosphine.…”

Section: Resultsmentioning

confidence: 99%

Pursuing the Complete OFF State in Photoswitchable Catalysis

Kravets,

Flaibani,

Szewczyk

et al. 2023

ACS Catal.

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Section: Resultsmentioning

confidence: 99%

Pursuing the Complete OFF State in Photoswitchable Catalysis

Kravets,

Flaibani,

Szewczyk

et al. 2023

ACS Catal.

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Olefin Metathesis, p‐Cresol, and the Second Generation Grubbs Catalyst: Fitting the Pieces

et al. 2021

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p‐Cresol as additive to the Grubbs second generation catalyst (GII) allows the cross‐metathesis of acrylates with prop‐1‐en‐1‐ylbenzenes under conditions that only give the prop‐1‐en‐1‐ylbenzene self‐metathesis product in the absence of cresol. NMR and IR spectroscopy, MALDI‐TOF MS and XPS supported the formation of a ruthenium benzylidene with hydrogen bonds between p‐cresol and the chloride ligands of GII. XPS furthermore confirmed p‐cresol to increase the binding energies of the GII Ru 3d5/2, 3d3/2, 3p3/2 and 3p1/2 photoelectron lines, whereas 1H NMR spectroscopy indicated the carbene carbon and hydrogen to be shielded. It is thus postulated that p‐cresol allows for more facile interaction between electron‐deficient compounds and the ruthenium benzylidene by decreasing the electron density on the metal center and increasing the electron density on the carbene.

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Functionalization of Ruthenium Olefin-Metathesis Catalysts for Interdisciplinary Studies in Chemistry and Biology

Matsuo

2021

Catalysts

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Hoveyda–Grubbs-type complexes, ruthenium catalysts for olefin metathesis, have gained increased interest as a research target in the interdisciplinary research fields of chemistry and biology because of their high functional group selectivity in olefin metathesis reactions and stabilities in aqueous media. This review article introduces the application of designed Hoveyda–Grubbs-type complexes for bio-relevant studies including the construction of hybrid olefin metathesis biocatalysts and the development of in-vivo olefin metathesis reactions. As a noticeable issue in the employment of Hoveyda–Grubbs-type complexes in aqueous media, the influence of water on the catalytic activities of the complexes and strategies to overcome the problems resulting from the water effects are also discussed. In connection to the structural effects of protein structures on the reactivities of Hoveyda–Grubbs-type complexes included in the protein, the regulation of metathesis activities through second-coordination sphere effect is presented, demonstrating that the reactivities of Hoveyda–Grubbs-type complexes are controllable by the structural modification of the complexes at outer-sphere parts. Finally, as a new-type reaction based on the ruthenium–olefin specific interaction, a recent finding on the ruthenium complex transfer reaction between Hoveyda–Grubbs-type complexes and biomolecules is introduced.

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Ligand Exchange Strategy for Delivery of Ruthenium Complex Unit to Biomolecules Based on Ruthenium–Olefin Specific Interactions

Cited by 4 publications

References 21 publications

Pursuing the Complete OFF State in Photoswitchable Catalysis

Pursuing the Complete OFF State in Photoswitchable Catalysis

Olefin Metathesis, p‐Cresol, and the Second Generation Grubbs Catalyst: Fitting the Pieces

Functionalization of Ruthenium Olefin-Metathesis Catalysts for Interdisciplinary Studies in Chemistry and Biology

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