Title
Targeting Valuable Chemical Commodities: Hydrazinemediated Diels-Alder Aromatization of Biobased Furfurals
Author
Cioc, R.C.
Crockatt, M.
van der Waal, J.C.
Bruijninckx, P.C.A.
Publication year
2022
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.
Subject
Energy
Sustainable Energy
Energy
To reference this document use:
http://resolver.tudelft.nl/uuid:bcec727d-b805-4700-94fa-7fb7ece4ae9c
DOI
https://doi.org/doi:cssc.202201139/
TNO identifier
976440
Publisher
Wiley, Heidelberg, Germany
Source
ChemSusChem
Document type
article