Direct Diels–Alder reactions of furfural derivatives with maleimides
Răzvan C Cioc
1, 2, 3, 4, 5, 6
,
Martin Lutz
4, 5, 7, 8, 9, 10
,
Evgeny A. Pidko
11, 12, 13, 14, 15, 16
,
Marc Crockatt
17, 18, 19, 20, 21
,
Jan C van der Waal
17
,
Pieter C. A. Bruijnincx
1, 2, 3, 4, 5, 6
2
Organic Chemistry and Catalysis
3
Debye Institute for NanoMaterials Science
4
Faculty of science
6
Universiteitsweg 99
8
Crystal and Structural Chemistry
9
Bijvoet Centre for Biomolecular Research
10
3584 CH Utrecht
|
12
Inorganic Systems Engineering
13
Department of Chemical Engineering
14
Faculty of Applied Sciences
16
2629 HZ Delft
|
18
Department of Sustainable Process and Energy Systems
19
TNO
20
2628 CA Delft
|
21
the Netherlands
|
Publication type: Journal Article
Publication date: 2021-01-01
scimago Q1
wos Q1
SJR: 1.928
CiteScore: 16.1
Impact factor: 9.2
ISSN: 14639262, 14639270
Environmental Chemistry
Pollution
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.
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61
Total citations:
61
Citations from 2025:
15
(24.59%)
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MLA
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GOST
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Cioc R. C. et al. Direct Diels–Alder reactions of furfural derivatives with maleimides // Green Chemistry. 2021. Vol. 23. No. 1. pp. 367-373.
GOST all authors (up to 50)
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Cioc R. C., Lutz M., Pidko E. A., Crockatt M., van der Waal J. C., Bruijnincx P. C. A. Direct Diels–Alder reactions of furfural derivatives with maleimides // Green Chemistry. 2021. Vol. 23. No. 1. pp. 367-373.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1039/D0GC03558K
UR - https://xlink.rsc.org/?DOI=D0GC03558K
TI - Direct Diels–Alder reactions of furfural derivatives with maleimides
T2 - Green Chemistry
AU - Cioc, Răzvan C
AU - Lutz, Martin
AU - Pidko, Evgeny A.
AU - Crockatt, Marc
AU - van der Waal, Jan C
AU - Bruijnincx, Pieter C. A.
PY - 2021
DA - 2021/01/01
PB - Royal Society of Chemistry (RSC)
SP - 367-373
IS - 1
VL - 23
SN - 1463-9262
SN - 1463-9270
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2021_Cioc,
author = {Răzvan C Cioc and Martin Lutz and Evgeny A. Pidko and Marc Crockatt and Jan C van der Waal and Pieter C. A. Bruijnincx},
title = {Direct Diels–Alder reactions of furfural derivatives with maleimides},
journal = {Green Chemistry},
year = {2021},
volume = {23},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://xlink.rsc.org/?DOI=D0GC03558K},
number = {1},
pages = {367--373},
doi = {10.1039/D0GC03558K}
}
Cite this
MLA
Copy
Cioc, Răzvan C., et al. “Direct Diels–Alder reactions of furfural derivatives with maleimides.” Green Chemistry, vol. 23, no. 1, Jan. 2021, pp. 367-373. https://xlink.rsc.org/?DOI=D0GC03558K.
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