Facile synthesis of 5-hydroxymethylfurfural: a sustainable raw material for the synthesis of key intermediates toward 21,23-dioxaporphyrins

Rajmohan, Rajamani; Gayathri, S.; Vairaprakash, Pothiappan

doi:10.1039/c5ra19400h

Cited by 21 publications

(17 citation statements)

References 59 publications

(77 reference statements)

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“…Previously, we have developed a facile method to access HMF from fructose at room temperature, utilizing silica as a solid support, mitigating humin formation, and facilitating selective extraction of HMF . Also, we have strategically utilized 2,4-dimethylpyrrole (DMP) in developing a colorimetric naked-eye chemosensor for copper(II) ions. , Here, we have utilized these two sustainable raw materials (HMF and DMP) in developing a sustainable photocatalyst with an objective to mitigate our dependency on fossil-based chemicals.…”

Section: Results and Discussionmentioning

confidence: 99%

5-Hydroxymethylfurfural-Derived Boron-Dipyrromethene Immobilized on Resin Support as a Sustainable Catalyst for C–H Arylation of Heterocycles

2019

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5-Hydroxymethylfurfural (HMF) was used as a sustainable raw material in the development of a resin-supported boron-dipyrromethene (BODIPY)-based photocatalyst. In the development of the catalyst, the brominated product (HMF-BODIPY-Br) and photocatalyst (HMF-BODIPY-Br-Suc) were isolated under a chromatography-free condition. The photocatalyst was loaded on polymeric resin by bridging alcohol functionality in HMF and amine functionality in polymeric resin using succinic anhydride. The resin-supported photocatalyst was used in light-mediated C–H arylation of various heterocycles using aryldiazonium salt. For representative examples, diazotization and photoarylation were carried out in one pot, and arylated furans were obtained in very good yields. C–H arylation was found to proceed via a photogenerated radical intermediate, and the radical intermediate was trapped by forming an adduct with TEMPO.

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Section: Results and Discussionmentioning

confidence: 99%

5-Hydroxymethylfurfural-Derived Boron-Dipyrromethene Immobilized on Resin Support as a Sustainable Catalyst for C–H Arylation of Heterocycles

2019

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“…The preparation of key intermediates of synthetic routes towards 21,23-dioxaporphyrins 185 from HMF was reported as an alternative to known but complex synthetic procedures, addressing drawbacks such as low yields and purification issues (Scheme 70). [207] The addition of a phenyl-Grignard reagent on HMF, or the Henry reaction with nitromethane gave access to the furylcarbinol 182 and nitroalkene 183 respectively in good yields. Those intermediates were then reacted with pyrrole under indium chloride catalysis to generate diversely substituted bis-heteroarylmethanes 184, highly valuable building-blocks for the preparation of 21,23dioxaporphyrins 185.…”

Section: Scheme 68 Solid-phase Combinatorial Synthesis Of Hmf-based mentioning

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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“…A variety of carbon‐extension reactions may be used to access >C6 building blocks from HMF (Scheme 7). Classical nucleophilic additions to the aldehyde group (aldol‐type reactions, [55] Grignard reactions [55d,56] or other organometallic additions [57] ) yielding polyfunctionalyzed furanic alcohols 21 are predominantly carried out with the use of protective groups at the hydroxyl substituent. However, some of these reactions may preserve free hydroxymethyl groups [55a,d,58] .…”

Section: Ab‐type Furanic Building Blocksmentioning

confidence: 99%

“…Classical nucleophilic additions to the aldehyde group (aldol‐type reactions, [55] Grignard reactions [55d,56] or other organometallic additions [57] ) yielding polyfunctionalyzed furanic alcohols 21 are predominantly carried out with the use of protective groups at the hydroxyl substituent. However, some of these reactions may preserve free hydroxymethyl groups [55a,d,58] . Allylic alcohol‐substituted derivatives 22 can be obtained via N ‐heterocyclic carbene‐catalyzed Baylis‐Hilman reaction [59]…”

Section: Ab‐type Furanic Building Blocksmentioning

confidence: 99%

The Increasing Value of Biomass: Moving From C6 Carbohydrates to Multifunctionalized Building Blocks via 5‐(hydroxymethyl)furfural

Galkin

Ananikov

2020

ChemistryOpen

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Recent decades have been marked by enormous progress in the field of synthesis and chemistry of 5‐(hydroxymethyl)furfural (HMF), an important platform chemical widely recognized as the “sleeping giant” of sustainable chemistry. This multifunctional furanic compound is viewed as a strong link for the transition from the current fossil‐based industry to a sustainable one. However, the low chemical stability of HMF significantly undermines its synthetic potential. A possible solution to this problem is synthetic diversification of HMF by modifying it into more stable multifunctional building blocks for further synthetic purposes.

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Facile synthesis of 5-hydroxymethylfurfural: a sustainable raw material for the synthesis of key intermediates toward 21,23-dioxaporphyrins

Abstract: In a simple and conceptually designed method for the dehydration of fructose on a solid support, 5-hydroxymethylfurfural (HMF) was synthesized in more than 95% isolated yield from fructose under very mild conditions at room temperature.

Cited by 21 publications

References 59 publications

5-Hydroxymethylfurfural-Derived Boron-Dipyrromethene Immobilized on Resin Support as a Sustainable Catalyst for C–H Arylation of Heterocycles

5-Hydroxymethylfurfural-Derived Boron-Dipyrromethene Immobilized on Resin Support as a Sustainable Catalyst for C–H Arylation of Heterocycles

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

The Increasing Value of Biomass: Moving From C6 Carbohydrates to Multifunctionalized Building Blocks via 5‐(hydroxymethyl)furfural

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