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Targeting Valuable Chemical Commodities: Hydrazine-mediated Diels-Alder Aromatization of Biobased Furfurals.
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- Additional Information
- Source:
Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 101319536 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1864-564X (Electronic) Linking ISSN: 18645631 NLM ISO Abbreviation: ChemSusChem Subsets: MEDLINE
- Publication Information:
Original Publication: Weinheim : Wiley-VCH
- Subject Terms:
- Abstract:
A hydrazine-mediated approach towards renewable aromatics production via Diels-Alder aromatization of readily available, biobased furfurals was explored as alterative to the more classical approaches that rely on reactive but uneconomical reduced dienes (e. g., 2,5-dimethylfuran). To enable cycloaddition chemistry with these otherwise unreactive formyl furans, substrate activation by N,N-dimethyl hydrazone formation was investigated. The choice of the reaction partner was key to the success of the transformation, and in this respect acrylic acid showed the most promising results in the synthesis of aromatics. This strategy allowed for selectivities up to 60 % for a complex transformation consisting of Diels-Alder cycloaddition, oxabridge opening, decarboxylation, and dehydration. Exploration of the furfural scope yielded generic structure-reactivity-stability relationships. The proposed methodology enabled the redox-efficient, operationally simple, and mild synthesis of renewable (p-disubstituted) aromatics of commercial importance under remarkably mild conditions.
(© 2022 The Authors. ChemSusChem published by Wiley-VCH GmbH.)
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- Grant Information:
741.018.408 Netherlands Organization for Scientific Research; Utrecht University's COVID-19
- Contributed Indexing:
Keywords: Diels-Alder; biomass conversion; cycloaddition; furfural; hydrazones
- Accession Number:
0 (Furans)
0 (Hydrazines)
0 (Hydrazones)
DJ1HGI319P (Furaldehyde)
- Publication Date:
Date Created: 20220714 Date Completed: 20220923 Latest Revision: 20230106
- Publication Date:
20240829
- Accession Number:
10.1002/cssc.202201139
- Accession Number:
35833422
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