A medium fluorous Grubbs–Hoveyda 2nd generation catalyst for phase transfer catalysis of ring closing metathesis reactions

Kobayashi, Yuki; Inukai, Sae; Kondo, Natsuki; Watanabe, Tomoko; Sugiyama, Yasumasa; Hamamoto, Hiromi; Shioiri, Takayuki; Matsugi, Masato

doi:10.1016/j.tetlet.2015.01.097

Cited by 22 publications

(12 citation statements)

References 26 publications

(3 reference statements)

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“…All commercial chemicals were used as received unless otherwise noted. Compounds 14, [33] 16, [34] 19, [35] and 21 [36] were prepared according to literature procedures. The following compounds have been previously described: 1, 2, and 3.…”

Section: General Informationmentioning

confidence: 99%

Ruthenium Complex Bearing a Hydroxy Group Functionalised N‐Heterocyclic Carbene Ligand – A Universal Platform for Synthesis of Tagged and Immobilised Catalysts for Olefin Metathesis

et al. 2021

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In memory of Klaus HafnerSix olefin metathesis catalysts, based on a common ruthenium precursor featuring a hydroxy-substituted N-heterocyclic carbene ligand, were successfully prepared and fully characterised. As proof-of-concept, two of them ([Ru] isonico and [Ru] dmab ) were directly immobilised on a solid support. These non-covalently heterogenised catalysts are efficient in different metathesis reactions and sufficiently stable to be used for repeated runs under batch and continuous flow conditions. In nonpolar media such as n-hexane, the catalytic character of the metathesis reactions is truly heterogeneous, and the contamination of the products with ruthenium is very low.

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Section: General Informationmentioning

confidence: 99%

Ruthenium Complex Bearing a Hydroxy Group Functionalised N‐Heterocyclic Carbene Ligand – A Universal Platform for Synthesis of Tagged and Immobilised Catalysts for Olefin Metathesis

et al. 2021

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“…In the field of ruthenium-alkylidene complexes, the influence of fluorine and fluorinated groups on their catalytic properties has been mainly studied by usage of definitely modified phosphine [41][42][43][44], benzylidene [45][46][47][48][49][50][51][52][53][54][55][56] ligands, as well as by the replacement of one or two chlorine atoms at ruthenium, for example, with perfluoro-carboxylates [57][58][59][60][61] and -alkoxylates [62,63].…”

Section: Figure 1 Commercially Available Olefin Metathesis Catalystsmentioning

confidence: 99%

Synthesis of metathesis catalysts with fluorinated unsymmetrical N,N’-diaryl imidazoline-based NHC ligands

Masoud

Topchiy

Peregudov

et al. 2017

Journal of Fluorine Chemistry

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“…RCM reactions using diethyl 2-allyl-2-(2-methylallyl)malonate 11 (8) were examined to confirm the relative catalytic activities of the prepared catalysts. The reactions were conducted with CDCl 3 as the solvent to allow NMR monitoring of the reaction aliquots.…”

Section: Figure 1 Second-generation Grubbs-hoveyda Catalystmentioning

confidence: 99%

Highly Activated Second-Generation Grubbs–Hoveyda Catalyst Driven by Intramolecular Steric Strain

Kobayashi

Miyazaki

Inukai

et al. 2016

Synlett

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Table of contents……………………………………………………………...…S1 I. Chemicals and instruments……………………………………………..……S2 II. Ring-closing metathesis reactions of 8 in CDCl 3 ……………………..……..S3 III. Ring-closing metathesis reactions of 10………………………………..……S3 IV. Synthesis of catalysts 1b-1g…………………………………………………S4-S19 V. UV-Vis spectrums of bidentate ligand precursors of 1f and 1g…………..…S20 VI. Noesy spectrums of 7f and 1f………………………………………………S21-S22 VII. Molecular orbital calculation (B3LYP/LAN2DZ)………………………..S23-S25 VIII. References………….………………………………………………………S26 IX. Spectral data for products…………………………………………………....S27-S61 S2 I. Chemicals and instruments All laboratory chemicals were purchased from Wako, TCI, Aldrich and Kanto Kagaku, used without further purification. Solvents were removed by rotary evaporation under reduced pressure using a 40 ºC water bath. Non-volatile compounds were dried in vacuo at 0.01 mbar. All reactions were stirred magnetically and monitored by thin layer chromatography (TLC) using silica gel plates. Purification by chromatography was performed on silica gel (45-75 µm). NMR spectra were recorded with JEOL

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A medium fluorous Grubbs–Hoveyda 2nd generation catalyst for phase transfer catalysis of ring closing metathesis reactions

Cited by 22 publications

References 26 publications

Ruthenium Complex Bearing a Hydroxy Group Functionalised N‐Heterocyclic Carbene Ligand – A Universal Platform for Synthesis of Tagged and Immobilised Catalysts for Olefin Metathesis

Ruthenium Complex Bearing a Hydroxy Group Functionalised N‐Heterocyclic Carbene Ligand – A Universal Platform for Synthesis of Tagged and Immobilised Catalysts for Olefin Metathesis

Synthesis of metathesis catalysts with fluorinated unsymmetrical N,N’-diaryl imidazoline-based NHC ligands

Highly Activated Second-Generation Grubbs–Hoveyda Catalyst Driven by Intramolecular Steric Strain

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