N-chelate ruthenium carbene complexes in olefin metathesis and isomerization

Shcheglova, N. M.; Kolesnik, V. D.; Ashirov, R. V.; Krasnokutskaya, E. A.

doi:10.1134/s1070428015070015

Cited by 5 publications

(1 citation statement)

References 8 publications

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“…Among all the donating elements listed above, with the exception of oxygen, chelates containing the ruthenium–nitrogen coordination bond and possessing both five- or six-membered rings ( 2 and 5 , Figure ) have been most extensively synthesized and investigated. − ,− A number of these N → Ru chelates have shown high catalytic activity in diverse olefin metathesis reactions, and further examination of their properties has provided valuable information about their stability. The stability can be increased by accurate adjustment of the substituents in the NR 2 group to almost eliminate moisture- and air-sensitivity, which are the main drawbacks shared by all commercially available O -containing metathesis catalysts.…”

Section: Introductionmentioning

confidence: 99%

Properties and Catalytic Activity of Hoveyda–Grubbs-Type Catalysts with an S → Ru Coordination Bond in a Six-Membered Chelate Ring

et al. 2023

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This work continues our group’s research into the synthesis and study of the catalytic activity of ruthenium chelates with various heteroatoms (O, S, N, and Se) in a six-membered ring. It was found that second-generation Hoveyda–Grubbs-type catalysts containing a sulfur-ruthenium coordinate bond in a six-membered chelate ring can be prepared easily and in high yields using standard procedures, based on the interaction between (2-vinylbenzyl)sulfanes and Ind II (the common precursor for Ru-complex synthesis). The obtained ruthenium derivatives, with a donor-acceptor S → Ru bond, can exist in two isomeric forms according to the arrangement of substituents around the central metal atom. Kinetically controlled trans-isomers are formed at temperatures below 80 °C in heptane and are less thermodynamically stable compared with cis-isomers, which arise under heating of trans-S-chelates in 1,2-dichloroethane at 110 °C. The structures of all the cis- and trans-isomers were determined and characterized in detail by X-ray diffraction and nuclear magnetic resonance. The study of the activity of the catalysts in standard ring-closing metathesis and ring-opening metathesis polymerization reactions showed that the cis-isomers are inactive in the absence of thermal or UV activation, while trans-complexes of the same type display excellent catalytic properties at r.t. that are superior to those of the commercially available HG-II catalyst. The structure, spectral characteristics, and catalytic activity of the catalysts containing an S → Ru bond in a six-membered chelate ring were compared with their five-membered analogues obtained in previous works.

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Section: Introductionmentioning

confidence: 99%

Properties and Catalytic Activity of Hoveyda–Grubbs-Type Catalysts with an S → Ru Coordination Bond in a Six-Membered Chelate Ring

et al. 2023

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An Efficient Synthesis of Chiral Non‐Racemic Hydroxyalkanoic Acids by Olefin Cross‐Metathesis Reactions

et al. 2018

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Cross-metathesis reactions of 1-hepten-3-ol, 1-octen-4-ol, 1octen-4-yl acetate and 1-tetradecen-4-ol with unsaturated methyl esters were investigated to optimize the synthesis of methyl hydroxyalkenoates, precursors of hydroxyalkanoic acids. Various commercially available catalysts, concentration ratios of reagents as well as microwave irradiation were explored. (R)-8hydroxydodecanoic acid and (S)-8-hydroxystearic acid were successfully obtained in 3 steps from enantiomerically enriched alcohols.

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The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2015

Herndon

2016

Coordination Chemistry Reviews

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N-chelate ruthenium carbene complexes in olefin metathesis and isomerization

Abstract: The catalytic activity of N-chelate ruthenium carbene complexes in the metathesis of hex-1-ene has been studied in comparison to the second generation Grubbs catalyst.

Cited by 5 publications

References 8 publications

Properties and Catalytic Activity of Hoveyda–Grubbs-Type Catalysts with an S → Ru Coordination Bond in a Six-Membered Chelate Ring

Properties and Catalytic Activity of Hoveyda–Grubbs-Type Catalysts with an S → Ru Coordination Bond in a Six-Membered Chelate Ring

An Efficient Synthesis of Chiral Non‐Racemic Hydroxyalkanoic Acids by Olefin Cross‐Metathesis Reactions

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2015

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