Solvent-Free Preparation of 5-(α-D-Glucosyloxymethyl)furfural from Isomaltulose–Choline Chloride Melts

Ruß, Carolin; Luff, Claudia; Begli, Alireza Haji; Koenig, Burkhard

doi:10.1080/00397911.2011.576375

Cited by 17 publications

(11 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…With respect to the Morita-Baylis-Hillman reaction, we have earlier investigated its application to HMF and its corresponding glucosylated analog GMF (Figure 1), available in one step from the commercial disaccharide isomaltulose. GMF, containing the furan, glucose and aldehydic entities, is able to undergo a remarkably wide range of transformations [44][45][46][47][48][49]. Strangely, applications of HMF and GMF in the Morita-Baylis-Hillman reaction were only scarcely investigated, though this route can afford interesting hydroxyacrylates with additional hydroxylated appendages.…”

Section: Introductionmentioning

confidence: 99%

Solvent issues in the Baylis-Hillman reaction of 5-hydroxymethyl furfural (HMF) and 5-glucosyloxymethyl furfural (GMF). Towards no-solvent conditions

Wang

Tan

Ahmar

et al. 2019

Pure and Applied Chemistry

View full text Add to dashboard Cite

The possibility to apply solventless conditions for the Baylis-Hillman reaction of 5-hydroxymethyl furfural (HMF) and its glucosylated analog, glucosyloxymethyl furfural (GMF) has been investigated. This study shows that highly functionalized adducts can be obtained in fair to good yields, under the conditions combining the renewability of the substrates, the straightforwardness of the strategy, and the lowered cost and toxicity of the solvent conditions. The issue of the polarity of the furanic substrate is addressed by comparing HMF with furfural and GMF.

show abstract

Section: Introductionmentioning

confidence: 99%

Solvent issues in the Baylis-Hillman reaction of 5-hydroxymethyl furfural (HMF) and 5-glucosyloxymethyl furfural (GMF). Towards no-solvent conditions

Wang

Tan

Ahmar

et al. 2019

Pure and Applied Chemistry

View full text Add to dashboard Cite

show abstract

“…Synthesis of functionalized pyrroles in ChCl/malonic acid.Another example for synthesis of annulated pyrroles(148) by three-component reaction between free sugars(146), amines and 1,3-dicarbonyl compounds(147) has been reported by Rokade and co-workers using ChCl/urea (Scheme 55) 106. The reaction may proceed via formation of intermediate enamines,generated in situ from amines and 1,3-dicarbonyl compounds.…”

mentioning

confidence: 99%

Recent advances in the application of deep eutectic solvents as sustainable media as well as catalysts in organic reactions

et al. 2015

View full text Add to dashboard Cite

Deep eutectic solvents (DESs), also known as deep eutectic ionic liquids (DEILs) or low-melting mixtures (LMMs) or low transition temperature mixtures (LTTMs) in the literature, have become more and more attractive in recent years due to their interesting properties and benefits, such as low cost of components, easy to prepare, tunable physicochemical properties, negligible vapor pressure, non-toxicity, biorenewability and biodegradability. These eutectic mixtures have been widely used as green and sustainable media as well as catalysts in many chemical processes. This review focuses on recent advances using DESs in organic reactions including addition reactions, cyclization reactions, replacement reactions, multicomponent reactions, condensation reactions, oxidation reactions, and reducing reactions.

show abstract

“…[164] Made from renewable resources, HMF is often seen as a platform chemical to replace petroleum-based materials. [165] The concept of applying a saccharide DES component as a reactant was also extended to the reaction of two components. Furthermore, the presence of an acidic catalyst in water can lead to rehydration and condensation of DMF, resulting in unwanted by-products.…”

Section: Application In Organic Synthesismentioning

confidence: 99%

Organic Synthesis without Conventional Solvents

Obst

König

2018

Eur J Org Chem

View full text Add to dashboard Cite

Organic synthesis without an organic solvent is still the exception. In this microreview, we discuss and compare different synthetic methods that proceed in the absence of conventional organic solvents. This includes solvent‐free methods in solids (mechanochemistry and solid‐state photochemistry), and in neat liquids (thermal and photocatalytic), as well as the application of unconventional solvents, such as ionic liquids and deep‐eutectic solvents. The different approaches are briefly introduced and examples illustrate their specific advantages, followed by a critical discussion of their limitations. Some methods have the intrinsic benefits of solvent‐free operation, such as avoiding solubility problems and side‐reactions with the solvent. However, every method has specific advantages and the demand of the synthetic application is crucial for selecting the best technique.

show abstract

Solvent-Free Preparation of 5-(α-D-Glucosyloxymethyl)furfural from Isomaltulose–Choline Chloride Melts

Cited by 17 publications

References 17 publications

Solvent issues in the Baylis-Hillman reaction of 5-hydroxymethyl furfural (HMF) and 5-glucosyloxymethyl furfural (GMF). Towards no-solvent conditions

Solvent issues in the Baylis-Hillman reaction of 5-hydroxymethyl furfural (HMF) and 5-glucosyloxymethyl furfural (GMF). Towards no-solvent conditions

Recent advances in the application of deep eutectic solvents as sustainable media as well as catalysts in organic reactions

Organic Synthesis without Conventional Solvents

Contact Info

Product

Resources

About