Print Email Facebook Twitter Direct Diels–Alder reactions of furfural derivatives with maleimides Title Direct Diels–Alder reactions of furfural derivatives with maleimides Author Cioc, R.C. Lutz, M. Pidko, E.A. Crockatt, M. van der Waal, J.C. Bruijninckx, P.C.A. Publication year 2021 Abstract The Diels–Alder (DA) reaction of furans is a versatile tool in synthetic organic chemistry and in the production of sustainable building blocks and smart materials. Numerous experimental and theoretical investigations suggest that the diene scope is effectively limited to electron-rich furans, which excludes the most abundant and readily accessible renewable derivatives: furfural and its 5-hydroxymethyl homologue. Herein we show for the first time that electron-poor 2-formylfurans can also directly engage in Diels–Alder couplings. The key to success is the use of aqueous medium, which supplies an additional thermodynamic driving force by coupling the unfavorable DA equilibrium to the exergonic hydration of the carbonyl functionality in the adducts to form geminal diols. This finding enables the direct access to various novel DA adducts derived from renewable furfurals and maleimides, via a mild, simple and environmentally-friendly synthetic protocol. Subject EnergyEnergy EfficiencyEnergy / Geological Survey Netherlands To reference this document use: http://resolver.tudelft.nl/uuid:18bfc90d-28ec-42f2-84b5-40bef5f86e11 TNO identifier 946978 Source Green Chemistry, 23 (23), 1-7 Document type article Files To receive the publication files, please send an e-mail request to TNO Library.