Microwave‐Assisted Ruthenium‐Catalysed Olefin Metathesis in Fluorinated Aromatic Hydrocarbons: A Beneficial Combination

Samojłowicz, C.; Borré, Etienne; Mauduit, Marc; Grela, Karol

doi:10.1002/adsc.201100053

Cited by 47 publications

(27 citation statements)

References 64 publications

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“…Further, the calculations indicated that C 6 F 6 interacts remarkably more strongly than C 6 H 6 , which is in line with the experimental results. Finally, there is no reason to rule out the possibility that the interactions described above could work co‐operatively 36…”

Section: Resultsmentioning

confidence: 99%

The Doping Effect of Fluorinated Aromatic Solvents on the Rate of Ruthenium‐Catalysed Olefin Metathesis

Samojłowicz

Bieniek

Pazio

et al. 2011

Chemistry A European J

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A study concerning the effect of using a fluorinated aromatic solvent as the medium for olefin metathesis reactions catalysed by ruthenium complexes bearing N‐heterocyclic carbene ligands is presented. The use of fluorinated aromatic hydrocarbons (FAH) as solvents for olefin metathesis reactions catalysed by standard commercially available ruthenium pre‐catalysts allows substantially higher yields of the desired products to be obtained, especially in the case of demanding polyfunctional molecules, including natural and biologically active compounds. Interactions between the FAH and the second‐generation ruthenium catalysts, which apparently improve the efficiency of the olefin metathesis transformation, have been studied by X‐ray structure analysis and computations, as well as by carrying out a number of metathesis experiments. The optimisation of reaction conditions by using an FAH can be regarded as a complementary approach for the design of new improved ruthenium catalysts. Fluorinated aromatic solvents are an attractive alternative medium for promoting challenging olefin metathesis reactions.

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Section: Resultsmentioning

confidence: 99%

The Doping Effect of Fluorinated Aromatic Solvents on the Rate of Ruthenium‐Catalysed Olefin Metathesis

Samojłowicz

Bieniek

Pazio

et al. 2011

Chemistry A European J

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“…Both catalysts showed high isolated yields of 23 , significantly outperforming the previously reported result, where under more harsh conditions (20 mol % Ru14 , C 6 F 5 CF 3 , MW, 120 °C) the desired product was isolated in 51% yield ( Scheme 3 a). 55 When challenging 4-methylene-1-tosylpiperidine ( 24 ) was employed with ( Z )-but-2-ene-1,4-diyl diacetate ( 22 ), the CM reaction afforded 25 in 86 or 75% yield, depending on the catalysts used. It shall be noted that the same substrate has been studied previously, giving with standard SIMes-based catalyst an almost twice lower yield (47%) of product 25 ( Scheme 3 b).…”

Section: Resultsmentioning

confidence: 99%

Sterically Tuned N-Heterocyclic Carbene Ligands for the Efficient Formation of Hindered Products in Ru-Catalyzed Olefin Metathesis

et al. 2020

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Formation of tetrasubstituted C–C double bonds via olefin metathesis is considered very challenging for classical Ru-based complexes. In the hope to improve this condition, three ruthenium olefin metathesis catalysts bearing sterically reduced N -heterocyclic carbene (NHC) ligands with xylyl “arms” were synthesized, characterized using both computational and experimental techniques, and tested in a number of challenging reactions. The catalysts are predicted to initiate much faster than the analogue with mesityl N -substituents. We also foreboded the rotation of xylyl side groups at ambient temperature and the existence of all four atropoisomers in the solution, which was in agreement with experimental data. These catalysts exhibited high activity at relatively low temperatures (45–60 °C) and at reduced catalyst loadings in various reactions of sterically hindered alkenes, including complex polyfunctional substrates of pharmaceutical interest, such as yangonin precursors, chrysantemic acid derivatives, analogues of cannabinoid agonists, α-terpineol, and finally a thermally unstable peroxide.

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“…Running the reaction under the standard conditions in dichloromethane or toluene under reflux, the desired cross-metathesis product α- 4a was isolated in low 10% and 3% yields ( Table 1 , entries 1 and 2). Although it has been observed that the use of octafluorotoluene [ 23 , 25 – 27 ] as the solvent had a positive effect on yields, its use provided α- 4a in a low 12% yield ( Table 1 , entry 3), but its use under microwave irradiation [ 26 , 28 – 30 ] gave rise to α- 4a in 33% isolated yield ( Table 1 , entry 4). A similar result (36% yield) was obtained with a 1:1 octafluorotoluene/ClCH 2 CH 2 Cl mixture ( Table 1 , entry 5).…”

Section: Resultsmentioning

confidence: 99%

Cross-metathesis reaction of α- and β-vinyl C-glycosides with alkenes

Šnajdr

Parkan

Hessler

et al. 2015

Beilstein J. Org. Chem.

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SummaryCross-metathesis of α- and β-vinyl C-deoxyribosides and α-vinyl C-galactoside with various terminal alkenes under different conditions was studied. The cross-metathesis of the former proceeded with good yields of the corresponding products in ClCH2CH2Cl the latter required the presence of CuI in CH2Cl2 to achieve good yields of the products. A simple method for the preparation of α- and β-vinyl C-deoxyribosides was also developed. In addition, feasibility of deprotection and further transformations were briefly explored.

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Microwave‐Assisted Ruthenium‐Catalysed Olefin Metathesis in Fluorinated Aromatic Hydrocarbons: A Beneficial Combination

Cited by 47 publications

References 64 publications

The Doping Effect of Fluorinated Aromatic Solvents on the Rate of Ruthenium‐Catalysed Olefin Metathesis

The Doping Effect of Fluorinated Aromatic Solvents on the Rate of Ruthenium‐Catalysed Olefin Metathesis

Sterically Tuned N-Heterocyclic Carbene Ligands for the Efficient Formation of Hindered Products in Ru-Catalyzed Olefin Metathesis

Cross-metathesis reaction of α- and β-vinyl C-glycosides with alkenes

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