ArticleGreen chemistry : an international journal and green chemistry resource : GC2021
Furoic acid and derivatives as atypical dienes in Diels-Alder reactions.
Article in Green chemistry : an international journal and green chemistry resource : GC, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 56 citations in OpenAlex.
- From Furfural to Reprocessable Thermosets: Diels-Alder Monomers for Dynamic Polyurethane Networks.ChemSusChem · 2026Review
- Tools for the Design of Diels-Alder-Based Reversible Polymer Systems: Reactivity and Reversibility of Furan/Maleimide Adducts.ACS omega · 2026Article
- Overcoming the Reversibility in the Diels-Alder Reaction of Bio-Based Electron-Poor Furans with Maleimides Through Liquid-to-Solid Phase Transition.International journal of molecular sciences · 2025Article
- Highly Strained Tricyclic Oxanorbornenes with Uncommon Reactivity Enable Rapid ROMP for Thermally High-Performing Polyenes.Macromolecules · 2025Article
- On the Valorisation of Chitin-Derived Furans by Milling.ChemSusChem · 2025Article
- C2 to C6 biobased carbonyl platforms for fine chemistry.Beilstein journal of organic chemistry · 2025Review
- Benzenoid Aromatics from Renewable Resources.Chemical reviews · 2024Review
- Article
- A Diels-Alder probe for discovery of natural products containing furan moieties.Beilstein journal of organic chemistry · 2024Article
- Efficient synthesis of fully renewable, furfural-derived building blocksGreen chemistry : an international journal and green chemistry resource : GC · 2023Article
- A DFT study on substituents, solvent, and temperature effect and mechanism of Diels-Alder reaction of hexafluoro-2-butyne with furan.Journal of molecular modeling · 2023Article
- Pd-catalyzed intermolecular consecutive double Heck reaction "on water" under air: facile synthesis of substituted indenes.RSC advances · 2023Article
- A Diamine-Oriented Biorefinery Concept Using Ammonia and Raney Ni as a Multifaceted Catalyst.Chemie-ingenieur-technik · 2022Article
- Clickable Polysaccharides for Biomedical Applications: A Comprehensive Review.Progress in polymer science · 2022Article
- Targeting Valuable Chemical Commodities: Hydrazine-mediated Diels-Alder Aromatization of Biobased Furfurals.ChemSusChem · 2022Article
- The Interplay between Kinetics and Thermodynamics in Furan Diels-Alder Chemistry for Sustainable Chemicals Production.Angewandte Chemie (International ed. in English) · 2022Review
- Chitosan Hydrogels Based on the Diels-Alder Click Reaction: Rheological and Kinetic Study.Polymers · 2022Article
- Diels-Alder Cycloaddition Reactions in Sustainable Media.Molecules (Basel, Switzerland) · 2022Review
- Monomers and Macromolecular Materials from Renewable Resources: State of the Art and Perspectives.Molecules (Basel, Switzerland) · 2021Review
- Intermolecular Diels-Alder Cycloadditions of Furfural-Based Chemicals from Renewable Resources: A Focus on the Regio- and Diastereoselectivity in the Reaction with Alkenes.International journal of molecular sciences · 2021Review
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 3 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The furan Diels-Alder (DA) cycloaddition reaction has become an important tool in green chemistry, being central to the sustainable synthesis of many chemical building blocks. The restriction to electron-rich furans is a significant limitation of the scope of suitable dienes, in particular hampering the use of the furans most readily obtained from biomass, furfurals and their oxidized variants, furoic acids. Herein, it is shown that despite their electron-withdrawing substituents, 2-furoic acids and derivatives (esters, amides) are in fact reactive dienes in Diels-Alder couplings with maleimide dienophiles. The reactions benefit from a substantial rate-enhancement when water is used as solvent, and from activation of the 2-furoic acids by conversion to the corresponding carboxylate salts. This approach enables Diels-Alder reactions to be performed under very mild conditions, even with highly unreactive dienes such as 2,5-furandicarboxylic acid. The obtained DA adducts of furoic acids are shown to be versatile synthons in the conversion to various saturated and aromatic carbocyclic products.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.