Eco-friendly synthesis of 5-hydroxymethylfurfural (HMF) and its application to the Ferrier-rearrangement reaction

Ding, Zekun; Luo, Xin; Ma, Yan; Chen, Heshan; Qiu, Saifeng; Sun, Guoxiang; Zhang, Wan; Yu, Chao; Wu, Zhenliang; Zhang, Jianbo

doi:10.1080/07328303.2018.1428990

Cited by 14 publications

(8 citation statements)

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“…The yield of compound 3d (entry 4) increased by 30% ( Dharuman et al, 2013 ). Our previous research found that 2,3-unsaturated glycoside of hydroxymethylfurfural (HMF), which is a significant platform compound and valuable molecule from biomass materials, showed promising antitumor activities ( Ding et al, 2018 ). Therefore, HMF was chosen as a special acceptor.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 2-Nitro-2,3-Unsaturated Glycosides by a Nanomagnetic Catalyst Fe3O4@C@Fe(III)

et al. 2022

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A sustainable magnetic core-shell nanocatalyst Fe3O4@C@Fe(III) was successfully applied in the synthesis of a series of 2-nitro-2,3-unsaturated O-glycosides with excellent yields (up to 89%) and high stereoselectivity (α:β > 19:1). The substrate ranges are widely applicable, including different kinds of alcohols and even structurally complex acceptors. In addition, phenols could be applied in good yields. Moreover, the catalyst could be easily separated from the reaction by the application of an external magnetic force and reused a minimum of five times without any significant decrease in catalytic performance.

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Section: Resultsmentioning

confidence: 99%

Synthesis of 2-Nitro-2,3-Unsaturated Glycosides by a Nanomagnetic Catalyst Fe3O4@C@Fe(III)

et al. 2022

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“…Esters of HMF with organic and inorganic acids also were prepared. Ferrier-type glycosylation of HMF was described recently utilizing different glycals …”

Section: Transformations Of 5-(hydroxymethyl)furfural (Hmf)mentioning

confidence: 99%

“…Ferrier-type glycosylation of HMF was described recently utilizing different glycals. 141 The reaction of HMF with alcohols can lead to ethers 142−144 or acetals 142,143,145 depending on the reaction conditions. In many cases, ethers are common byproducts in catalytic hydrogenation of HMF in alcoholic media.…”

Section: Transformations Of 5-(hydroxymethyl)furfural (Hmf)mentioning

confidence: 99%

Chemical Transformations of Biomass-Derived C6-Furanic Platform Chemicals for Sustainable Energy Research, Materials Science, and Synthetic Building Blocks

Kucherov

Romashov

Galkin

et al. 2018

ACS Sustainable Chem. Eng.

271

219

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Recent advances in the area of biomass-derived C6-furanic platform chemicals for sustainable biomass processing are analyzed focusing on chemical reactions important for development of practical applications and materials science. Among the chemical processes currently being studied, tuning the amount of oxygen-containing functional groups remains the most active research direction. Production of efficient fuels requires the removal of oxygen atoms (reduction reactions), whereas utilization of biomass-derived furanic derivatives in material science points out the importance of oxidation in order to form dicarboxylic derivatives. Stimulated by this driving force, oxidation and reduction of 5-(hydroxymethyl)furfural (HMF) are nowadays massively studied. Moreover, these fundamental transformations are often used as model reactions to test new catalysts, and HMF transformations guide the development of new catalytic systems. From the viewpoint of organic synthesis, highly diverse chemical reactivity is explored and a number of bioderived synthetic building blocks with different functional groups are now accessible. This Perspective covers the most recent literature (since Jan 2017) to highlight the emerging research trends.

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“…More recently, Zhang described the transformation of various glycals including 120 with HMF in the presence of FeCl 3 .6H 2 O/C as a recyclable catalyst in DCE, leading to a range of 2,3-unsaturated glycosides in 67-92% yields. [149] Other carbohydrate derivatives of HMF have also been studied. Cottier investigated several possible pathways to prepare -glucosylmethylfurfural 123 starting from HMF and glycosyl donors such as 122.…”

Section: Scheme 47 Alkoxylation Of 3-imidoallenylphosphonate With 5-hmfmentioning

confidence: 99%

5-Hydroxymethylfurfural (HMF) in Organic Synthesis: A Review of its Recent Applications Towards Fine Chemicals

Fan

Verrier

Queneau

et al. 2019

COS

104

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Background: 5-Hydroxymethylfurfural (5-HMF) is a biomass-derived platform chemical, which can be produced from carbohydrates. In the past decades, 5- HMF has received tremendous attention because of its wide applications in the production of various value-added chemicals, materials and biofuels. The manufacture and the catalytic conversion of 5-HMF to simple industrially-important bulk chemicals have been well reviewed. However, employing 5-HMF as a building block in organic synthesis has never been summarized exclusively, despite the rapid development in this area. Objective: The aim of this review is to bring a fresh perspective on the use of 5-HMF in organic synthesis, to the exclusion of already well documented conversion of 5-HMF towards relatively simple molecules such as 2,5-furandicarboxylic acid, 2,5-dimethylfuran and so on notably used as monomers or biofuels. Conclusion: As it has been shown throughout this review, 5-HMF has been the object of numerous studies on its use in fine chemical synthesis. Thanks to the presence of different functional groups on this platform chemical, it proved to be an excellent starting material for the preparation of various fine chemicals. The use of this C-6 synthon in novel synthetic routes is appealing, as it allows the incorporation of renewable carbonsources into the final targets.

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Eco-friendly synthesis of 5-hydroxymethylfurfural (HMF) and its application to the Ferrier-rearrangement reaction

Cited by 14 publications

References 50 publications

Synthesis of 2-Nitro-2,3-Unsaturated Glycosides by a Nanomagnetic Catalyst Fe3O4@C@Fe(III)

Synthesis of 2-Nitro-2,3-Unsaturated Glycosides by a Nanomagnetic Catalyst Fe3O4@C@Fe(III)

Chemical Transformations of Biomass-Derived C6-Furanic Platform Chemicals for Sustainable Energy Research, Materials Science, and Synthetic Building Blocks

5-Hydroxymethylfurfural (HMF) in Organic Synthesis: A Review of its Recent Applications Towards Fine Chemicals

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