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Updated: Oct 8, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Tandem Diels-Alder Cycloaddition/Aromatization of Biomass-Derived 2-Methylfuran Toward Renewable
Hui-Tong Hu1, Ze-Kuan Zhang1, Tian-Jun Gong1
1Anhui Province Key Laboratory of Biomass Chemistry, CAS Key Laboratory of Urban Pollutant Conversion, University of Science and Technology of China, Hefei, China.
Abstract:
Biomass holds significant promise as a sustainable feedstock for replacing petrochemical products in green chemical synthesis. Among biomass-derived molecules, furan serves as a key building block for constructing diverse, high-value bioactive molecules. Herein, this study presents a highly chemoselective and regioselective Diels-Alder (D-A) reaction between biomass-derived monosubstituted furans and acrylamides, followed by aromatization, enabling the efficient synthesis of the bioactive molecule N,N-Diethyl-3-methylbenzamide (DEET) with excellent selectivity. Notably, the catalyst (Hf(OTf)4) serves not only as the Lewis acid center but also as a conformation-directing template and intermediate stabilizer in this reaction. Gram-scale syntheses were performed in both tubular and continuous-flow reactors, confirming the scalability of this process. This methodology offers broad applicability for the regioselective synthesis of multisubstituted aromatic products from biomass-derived furans, providing a novel approach for the high-value conversion of biomass into bioactive molecules.
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