Journal
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 10, Issue 38, Pages 12602-12612Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.2c03209
Keywords
HMF; active methylene; boric acid; hydrotalcite; solvent free
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Funding
- Universidad Pedagogica y Tecnologica de Colombia
- Universidad de los Andes
- Vicerrectoria de Investigaciones-UPTC
- Departamento de Quimica and Facultad de Ciencias at the Universidad de los Andes, Colombia [FAPA-P18.160422.043, INV-201984-1800]
- CONICET [PIP 0111]
- Agencia Nacional de Promocion Cientifica y Tecnica ANPCyT [0157]
- UNLP
- RUDN University Strategic Academic Leadership Program
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This study describes the use of boric acid deposited on hydrotalcite as a catalyst for the Knoevenagel reaction between HMF derivatives and active methylene compounds. The catalyst showed high activity, good selectivity, and could be reused multiple times without significant loss of activity.
5-Hydroxymethylfurfural (HMF) is a well-known platform chemical derivative from biomass. Herein, we described the application of boric acid deposited on hydrotalcite as a catalyst in the Knoevenagel reaction of HMF derivatives and active methylene compounds to afford new HMF derivatives containing an acrylonitrile moiety under solvent-free conditions. The boric acid incorporation method on hydrotalcite conditioned the yields obtained because the aluminum substitution by boron atoms can modify the acidity of these solids. The Knoevenagel adduct structure (3a) was studied and confirmed by X-ray crystallography. This protocol synthesis features operational simplicity, short reaction times, high yields, good to excellent (E)-isomer selectivity, and low catalyst loading. Remarkably, the catalyst could be simply recovered and reused up to five cycles without appreciable loss of catalytic activity.
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