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Slowly does it! By adding the substrate by a syringe pump, a highly efficient Friedel-Crafts reaction of 4,7-dihydroindoles with nitroolefins was realized with 0.5 mol % of a chiral phosphoric acid. The Friedel-Crafts alkylation, together with a subsequent oxidation of the product, led to 2-substituted indoles in excellent enantiomeric excesses, which can be easily transformed to enantioenriched tetrahydro-gamma-carbolines.
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http://dx.doi.org/10.1002/chem.200900033 | DOI Listing |
Carbohydr Polym
November 2025
Frontiers Science Center for Deep Ocean Multispheres and Earth System, Key Laboratory of Marine Chemistry Theory and Technology Ministry of Education Ocean University of China, Qingdao 266100, China; Sanya Oceanographic Institution Ocean University of China, Sanya 572024, China. Electronic address:
Developing three-dimensional composite materials with high adsorption capacity, environmentally friendliness, and facile processability is essential for removing organic dyes from wastewater and enhancing ecological protection. In this study, a Friedel-Crafts alkylation reaction was employed to introduce multiple double bonds into the benzene ring of dopamine hydrochloride monomer, resulting in dopamine triacrylamide (DAHAM) compounds. Dopamine triacrylamide crosslinked chitosan (CTS)/polyacrylic acid (PAA) cryogels (CTS/PAA@DAHAM) were prepared to achieve efficient and specific adsorption of anionic dyes.
View Article and Find Full Text PDFBioresour Technol
September 2025
Department of Chemistry, National Institute of Technology Karnataka, Surathkal, Mangalore 575025 Karnataka, India. Electronic address:
Efficient conversion of biomass into hydrocarbon fuels, organic chemicals, and synthetic polymers promises sustainability of the organic chemical industries and a circular carbon economy. Synthesizing targeted bioproducts bearing more carbon atoms in their skeletal system than the parent carbohydrate molecules require strategic use of various CC bond-forming reactions (e.g.
View Article and Find Full Text PDFRSC Adv
August 2025
Laboratoire de Développement Chimique, Galénique et Pharmacologique des Médicaments, Faculté de Pharmacie de Monastir, Université de Monastir Rue Avicenne 5000 Monastir Tunisia
The Friedel-Crafts acylation of arenes is a fundamental reaction extensively employed in both academic research and industrial applications. A significant limitation of this reaction is the requirement for stoichiometric amounts of Lewis acid catalysts, which are typically sensitive and generate considerable waste. In this study, we present an improved catalytic approach for the Friedel-Crafts acylation of activated arenes.
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August 2025
Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University 3-3-35 Yamate-cho Suita Osaka 564-8680 Japan
Alginate- and -carrageenan-supported imidazolidinone catalysts were newly prepared, and their catalytic activities for the Friedel-Crafts alkylation of 1-methylindole with crotonaldehyde were evaluated. The enantiomeric excess of the product was enhanced by using the polymer-supported catalysts consisting of an appropriate absolute configuration of imidazolidinones and alginate/-carrageenan the cooperative effect that constructs a chiral environment more suited for asymmetric induction compared to imidazolidinone only. Further, the polymer-supported catalysts were easily removed from the reaction media by a simple filtration technique.
View Article and Find Full Text PDFJ Org Chem
September 2025
Universidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Departamento de Ciencias Químicas, Buenos Aires CP 1113AAD, Argentina.
A series of 3-hydroxykynurenic acid derivatives bearing a halogen atom in different positions are synthesized by hydroamination of methyl acetylenedicarboxylate with haloanilines, in an aza-Michael type reaction. Subsequent heterocyclization with Eaton's reagent yields halo-substituted kynurenic acid (KA) methyl esters via an intramolecular Friedel-Crafts reaction. Finally, the hydroxylation is achieved by the Elbs oxidation.
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