Efficient synthesis of fully renewable, furfural-derived building blocks via formal Diels-Alder cycloaddition of atypical addends
Diels-Alder (DA) cycloaddition of furanics is emerging as a key transformation in circular chemistry, providing access to highly versatile, biobased platform molecules. Further development of this technology into viable industrial applications faces major challenges, a notorious one being the lack o...
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| Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC Jg. 25; H. 23; S. 9689 |
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| Hauptverfasser: | , , , |
| Format: | Journal Article |
| Sprache: | Englisch |
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27.11.2023
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| ISSN: | 1463-9262 |
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| Abstract | Diels-Alder (DA) cycloaddition of furanics is emerging as a key transformation in circular chemistry, providing access to highly versatile, biobased platform molecules. Further development of this technology into viable industrial applications faces major challenges, a notorious one being the lack of reactivity of the most readily available furans, i.e. the furfural derivatives. Herein we describe the remarkably-facile intramolecular DA reaction of allyl acetals of different furfurals to efficiently afford formal DA adducts with the atypical, unreactive dienophile allyl alcohol. Our methodology gives access to unprecedented oxanorbornene derivatives in high chemo-, regio- and stereoselectivity, which can be readily diversified into valuable products. This offers the potential of scalable production of renewable chemical building blocks from cheap, bioderived platform molecules.Diels-Alder (DA) cycloaddition of furanics is emerging as a key transformation in circular chemistry, providing access to highly versatile, biobased platform molecules. Further development of this technology into viable industrial applications faces major challenges, a notorious one being the lack of reactivity of the most readily available furans, i.e. the furfural derivatives. Herein we describe the remarkably-facile intramolecular DA reaction of allyl acetals of different furfurals to efficiently afford formal DA adducts with the atypical, unreactive dienophile allyl alcohol. Our methodology gives access to unprecedented oxanorbornene derivatives in high chemo-, regio- and stereoselectivity, which can be readily diversified into valuable products. This offers the potential of scalable production of renewable chemical building blocks from cheap, bioderived platform molecules. |
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| AbstractList | Diels-Alder (DA) cycloaddition of furanics is emerging as a key transformation in circular chemistry, providing access to highly versatile, biobased platform molecules. Further development of this technology into viable industrial applications faces major challenges, a notorious one being the lack of reactivity of the most readily available furans, i.e. the furfural derivatives. Herein we describe the remarkably-facile intramolecular DA reaction of allyl acetals of different furfurals to efficiently afford formal DA adducts with the atypical, unreactive dienophile allyl alcohol. Our methodology gives access to unprecedented oxanorbornene derivatives in high chemo-, regio- and stereoselectivity, which can be readily diversified into valuable products. This offers the potential of scalable production of renewable chemical building blocks from cheap, bioderived platform molecules.Diels-Alder (DA) cycloaddition of furanics is emerging as a key transformation in circular chemistry, providing access to highly versatile, biobased platform molecules. Further development of this technology into viable industrial applications faces major challenges, a notorious one being the lack of reactivity of the most readily available furans, i.e. the furfural derivatives. Herein we describe the remarkably-facile intramolecular DA reaction of allyl acetals of different furfurals to efficiently afford formal DA adducts with the atypical, unreactive dienophile allyl alcohol. Our methodology gives access to unprecedented oxanorbornene derivatives in high chemo-, regio- and stereoselectivity, which can be readily diversified into valuable products. This offers the potential of scalable production of renewable chemical building blocks from cheap, bioderived platform molecules. |
| Author | Bruijnincx, Pieter C A Cioc, Răzvan C Harsevoort, Eva Lutz, Martin |
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| CitedBy_id | crossref_primary_10_1016_j_ijbiomac_2025_143681 crossref_primary_10_1016_j_cattod_2024_114726 crossref_primary_10_1021_acs_macromol_4c02601 crossref_primary_10_1039_D5GC00006H crossref_primary_10_1016_j_cogsc_2025_101002 crossref_primary_10_1021_jacs_4c12678 crossref_primary_10_1016_S1872_2067_25_64765_6 crossref_primary_10_1039_D4QO01114G |
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