Heteromacrocycles from Ring-Closing Metathesis of Unsaturated Furanic Ethers

Cottier, Louis; Descotes, G.; Soro, Yaya

doi:10.1081/scc-120026858

Cited by 44 publications

(21 citation statements)

References 17 publications

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“…Among them, the reduction of the formyl group of HMF to afford the symmetrical diol 2,5‐bis(hydroxymethyl)furan (BHMF), has received much attention . BHMF finds a wide range of applications as a building block for polymers, foams, and crown ethers, and as intermediate in pharmaceuticals . It can also be converted into biofuel additives such as 2,5‐dimethylfuran and 2,5‐dimethyltetrahydrofuran .…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Synthesis of 5‐Hydroxymethylfurfural (HMF)‐Derived Plasticizers by Coupling HMF Reduction with Enzymatic Esterification

et al. 2020

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Biobased plasticizers, as substitutes for phthalates, have been synthesized from 5‐hydroxymethylfurfural (HMF) and carboxylic acids (or esters) through a chemoenzymatic cascade process that involves as its first step the reduction of 5‐hydroxymethylfurfural into 2,5‐bis(hydroxymethyl)furan (BHMF), followed by the esterification of BHMF with carboxylic acids (or esters) by using a supported lipase (Novozym 435). The reduction of HMF into BHMF is performed by using monodisperse metallic Co nanoparticles with a thin carbon shell (Co@C) with high activity and selectivity. After optimization of reaction conditions (temperature, hydrogen pressure, and solvent), it is possible to achieve 97 % conversion of HMF with 99 % selectivity to BHMF after 2 h reaction time. The reduction of HMF and esterification of BHMF using carboxylic acids or vinyl esters as acyl donors by lipase are optimized separately in batch and in fixed‐bed continuous reactors. The coupling of two flow reactors (for reduction and subsequent esterification) working under optimized reaction conditions affords the diesters of BHMF in roughly 90 % yield with no loss of activity during 60 h of operation.

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Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Synthesis of 5‐Hydroxymethylfurfural (HMF)‐Derived Plasticizers by Coupling HMF Reduction with Enzymatic Esterification

et al. 2020

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“…In addition, HMF could be transformed into 2,5‐bis(hydroxymethyl)furan (BHMF), 2,5‐dihydroxymethyltetrahydrofuran (DHMTHF), and 2,5‐dimethylfuran (DMF) through selective reduction . BHMF is the hydrogenation product of the formyl group in HMF and is a versatile building block for the synthesis of polymers, drugs, macrocycle polyether compounds, and crown ethers …”

Section: Introductionmentioning

confidence: 99%

Biocatalytic Reduction of HMF to 2,5‐Bis(hydroxymethyl)furan by HMF‐Tolerant Whole Cells

Zhang

et al. 2016

ChemSusChem

100

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What is the most significant result of this study? The most importanto bservation of this study is the biocata-lyst-Meyerozyma guilliermondii SC1103-since the cells of this yeast are much more tolerant to 5-hydroxymethylfurfural (HMF) compared to microbesr eported previously.I na ddition, the efficiency of the biocatalytic HMF reduction as well as its selectivity are very high. What new scientific questions/problems doest his work raise? We think that one of the new scientific questionsm ay be the mechanism by which this yeast strain can tolerate high levels of HMF.U nderstandingt his mechanism will provideu seful in-formationf or the rational modificationo ft he strains for various applications involving HMF. What is the story behindt he cover? The yeast train plays ad ominant role in the biocatalytic reduction of HMF,w hich earned the title of the conductor.G lucose, fructose(the precursors for the synthesis of HMF), HMF,a nd 2,5-bis(hydroxymethyl)furan act as the piano players. So we named this cover image "TheConductor and Its Players". Invited for this month'sc over is the group of Min-Hua Zong at South ChinaU niversity of Technology.T he image shows the selectives ynthesis of 2,5-bis(hydroxymethyl)furan from 5-hydroxymethylfurfural (HMF) using highly HMF-tolerantw hole cells.

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“…FDM has been identified as a useful building block in the synthesis of macromolecules 8. Stoichiometric reduction of HMF with a twofold excess of sodium borohydride leads to FDM in 97 % yield 9. Catalytic approaches are more attractive and several examples have already been reported.…”

Section: Introductionmentioning

confidence: 99%

Tunable and Selective Conversion of 5‐HMF to 2,5‐Furandimethanol and 2,5‐Dimethylfuran over Copper‐Doped Porous Metal Oxides

et al. 2014

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Tunable and selective hydrogenation of the platform chemical 5-hydroxymethylfurfural into valuable C6 building blocks and liquid fuel additives is achieved with copper-doped porous metal oxides in ethanol. A new catalyst composition with improved hydrogenation/hydrogenolysis activity is obtained by introducing small amounts of ruthenium dopant into the previously reported Cu(0.59) Mg2.34 Al1.00 structure. At a mild reaction temperature (100 °C), 2,5-furandimethanol is obtained with excellent selectivity up to >99%. Higher reaction temperatures (220 °C) favor selective deoxygenation to 2,5-dimethylfuran and minor product 2,5-dimethyltetrahydrofuran with a combined yield as high as 81%. Notably, these high product yields are maintained at a substrate concentration up to 10 wt% and a low catalyst loading. The influence of different alcohol solvents on product selectivity is explored. Furthermore, reaction intermediates formed at different reaction temperatures are identified. The composition of these product mixtures provides mechanistic insight into the nature of the reduction pathways that influence product selectivity. The catalysts are characterized by elemental analysis, TEM, and BET techniques before and after the reaction. Catalyst recycling experiments are conducted in batch and in a continuous-flow setup.

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Heteromacrocycles from Ring-Closing Metathesis of Unsaturated Furanic Ethers

Cited by 44 publications

References 17 publications

Chemoenzymatic Synthesis of 5‐Hydroxymethylfurfural (HMF)‐Derived Plasticizers by Coupling HMF Reduction with Enzymatic Esterification

Chemoenzymatic Synthesis of 5‐Hydroxymethylfurfural (HMF)‐Derived Plasticizers by Coupling HMF Reduction with Enzymatic Esterification

Biocatalytic Reduction of HMF to 2,5‐Bis(hydroxymethyl)furan by HMF‐Tolerant Whole Cells

Tunable and Selective Conversion of 5‐HMF to 2,5‐Furandimethanol and 2,5‐Dimethylfuran over Copper‐Doped Porous Metal Oxides

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