Recent advances in applications of vinyl ether monomers for precise synthesis of custom-tailored polymers

Kirillov, Evgueni; Rodygin, Konstantin S.; Ananikov, Valentine P.

doi:10.1016/j.eurpolymj.2020.109872

Cited by 42 publications

(38 citation statements)

References 268 publications

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“…The nucleophilic addition proceeds under superbasic conditions in good yields without the use of gaseous acetylene and can be safely carried out in a laboratory. Labeled compounds with deuterium [21] and carbon 13 C [22] incorporation can also be obtained that increase applications in further transformations: polymerization [23], Heck-like reactions [24], cycloaddition [25,26], and many others. Here, we expand the scope of applications of vinyl derivatives and demonstrate that molecular hydrogen can be successfully added to functionalized vinyl derivatives.…”

Section: Introductionmentioning

confidence: 99%

Sustainable Hydrogenation of Vinyl Derivatives Using Pd/C Catalysts

Mironenko¹,

Saybulina²,

Степанова³

et al. 2021

Catalysts

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The hydrogenation of unsaturated double bonds with molecular hydrogen is an efficient atom-economic approach to the production of a wide range of fine chemicals. In contrast to a number of reducing reagents typically involved in organic synthesis, hydrogenation with H2 is much more sustainable since it does not produce wastes (i.e., reducing reagent residues). However, its full sustainable potential may be achieved only in the case of easily separable catalysts and high reaction selectivity. In this work, various Pd/C catalysts were used for the liquid-phase hydrogenation of O-, S-, and N-vinyl derivatives with molecular hydrogen under mild reaction conditions (room temperature, pressure of 1 MPa). Complete conversion and high hydrogenation selectivity (>99%) were achieved by adjusting the type of Pd/C catalyst. Thus, the proposed procedure can be used as a sustainable method for vinyl group transformation by hydrogenation reactions. The discovery of the stability of active vinyl functional groups conjugated with heteroatoms (O, S, and N) under hydrogenation conditions over Pd/C catalysts opens the way for many useful transformations.

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Section: Introductionmentioning

confidence: 99%

Sustainable Hydrogenation of Vinyl Derivatives Using Pd/C Catalysts

Mironenko¹,

Saybulina²,

Степанова³

et al. 2021

Catalysts

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“…An advanced cycloaddition strategy with a solid source of the C 2 alkyne unit from CaC 2 was also tested. Recently, calcium carbide was involved in the synthesis of vinyl ethers 33 valuable monomers 34 and other various synthetic appli-cations. 35 Evaluation of the possibility of the use of gaseous alkynes in electrochemically promoted synthesis of triazoles was of much interest.…”

Section: Catalytic Applications Of a Solution Of Electrochemically Generated Copper Catalyst In Ilsmentioning

confidence: 99%

Generation, regeneration, and recovery of Cu catalytic system by changing the polarity of electrodes

et al. 2022

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“…Nucleophilic additions to the carbide‐derived acetylene provide access to a range of O‐,S‐ and N‐vinyl derivatives (path G), which are valuable units for polymeric materials. [ 21 ] Reactions of CaC 2 with disulfides and diselenides afford S‐ and Se‐containing molecules (path H). The carbide‐induced synthesis of 2‐methylbenzofurans (path I) and Diels‐Alder reactions (path J) are available as well.…”

Section: A Map Of Calcium Carbide Synthetic Transformationsmentioning

confidence: 99%

Calcium Carbide: Versatile Synthetic Applications, Green Methodology and Sustainability

et al. 2020

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Acetylene is a key building block for organic chemistry and potentially can be involved in a diverse range of synthetic transformations. However, critical analysis of practical considerations showed that application of gaseous acetylene in regular synthetic labs encounters a number of difficulties. Safety limitations due to flammable and explosive nature of gaseous acetylene and requirements for specialized high‐pressure equipment impose serious drawbacks. Typical reaction conditions involve excess of gaseous reactant, which is simply released to the atmosphere at the end of the reaction, thus generating waste and causing contamination. Calcium carbide brings a new green and sustainable wave into powerful alkyne transformations and significantly expands the repertoire of traditional acetylene chemistry. The novel trend of using calcium carbide instead of gaseous acetylene is synthetically beneficial and opens a novel reactivity for the C≡C unit. This review highlights recent advances in carbide chemistry, demonstrates its advantages and prospects in term of green synthetic approach.

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Recent advances in applications of vinyl ether monomers for precise synthesis of custom-tailored polymers

Cited by 42 publications

References 268 publications

Sustainable Hydrogenation of Vinyl Derivatives Using Pd/C Catalysts

Sustainable Hydrogenation of Vinyl Derivatives Using Pd/C Catalysts

Generation, regeneration, and recovery of Cu catalytic system by changing the polarity of electrodes

Calcium Carbide: Versatile Synthetic Applications, Green Methodology and Sustainability

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