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.
| Original language | English |
|---|---|
| Pages (from-to) | 367-373 |
| Number of pages | 7 |
| Journal | Green Chemistry |
| Volume | 23 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 7 Jan 2021 |
Bibliographical note
Funding Information:This work was supported by The Netherlands Organization for Scientific Research (NWO LIFT grant 741.018.408). NWO is acknowledged for providing access to SurfSARA supercomputing facilities. E.A. Pidko acknowledges funding from the European Research Council (ERC) under the European Union's Horizon 2020 research and innovation programme (grant agreement no. 725686). The X-ray diffractometer has been financed by NWO. Dr T.N. Ran and Dr J. T. B. H. Jastrzebski (Utrecht University) and Mr I. Chernyshov (ITMO University, St. Petersburg) are acknowledged for technical assistance.
Funding Information:
This work was supported by The Netherlands Organization for Scientific Research (NWO LIFT grant 741.018.408). NWO is acknowledged for providing access to SurfSARA supercomputing facilities. E.A. Pidko acknowledges funding from the European Research Council (ERC) under the European Union’s Horizon 2020 research and innovation programme (grant agreement no. 725686). The X-ray diffractometer has been financed by NWO. Dr T.N. Ran and Dr J. T. B. H. Jastrzebski (Utrecht University) and Mr I. Chernyshov (ITMO University, St. Petersburg) are acknowledged for technical assistance.
Publisher Copyright:
© The Royal Society of Chemistry.
