Arylisonitriles (2 equivalents) react with alkyl and perfluoroalkyl radicals to form 2-alkylated indole-3-imines via two sequential additions to the isonitrile moiety followed by homolytic aromatic substitution. The three component reaction comprises three C-C bond formations. The endocyclic imine functionality in the products is more reactive in follow up chemistry and hydrolysis of the exocyclic imine leads to 3-oxindoles that show fluorescence properties.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c6cc02284g | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
The impact of anions on electrooxidation of perfluoroalkyl acids by porous Magnéli phase titanium suboxide anodes.
PLoS One
January 2025
Department of Crop and Soil Sciences, College of Agricultural and Environmental Sciences, University of Georgia, Griffin, Georgia, United States of America.
Previous studies have indicated the great performance of electrooxidation (EO) to mineralize per- and polyfluoroalkyl substances (PFASs) in water, but different anions presented in wastewater may affect the implementation of EO treatment in field applications. This study invetigated EO treatment of perfluorooctane sulfonate (PFOS) and perfluorooctanoic acid (PFOA), two representative perfluoroalkyl acids (PFAAs), using porous Magnéli phase titanium suboxide anodes in electrolyte solutions with different anions present, including NO3-, SO42-, CO32- and PO43-. The experiment results indicate that CO32- enhanced PFAS degradation, while NO3- suppressed the degradation reactions with its concentration higher than 10 mM.
View Article and Find Full Text PDFUnveiling the Contribution of Hydrogen Radicals to Per- and Polyfluoroalkyl Substances (PFASs) Defluorination: Applicability and Degradation Mechanisms.
Environ Sci Technol
January 2025
Key Laboratory of Pollution Processes and Environmental Criteria, Ministry of Education, Tianjin Key Laboratory of Environmental Remediation and Pollution Control, College of Environmental Science and Engineering, Nankai University, Tianjin 300071, PR China.
At present, the defluorination of per- and polyfluoroalkyl substances (PFASs), including perfluoroether compounds as substitutes of perfluorooctanoic acid (PFOA) and perfluorooctanesulfonate, is limited by the effective active species produced during the oxidation-reduction process. The contribution of the hydrogen radical (•H) as a companion active substance in the photoreduction and electrocatalytic degradation of PFASs has been neglected. Herein, we demonstrate that perfluorocarboxylic acids and perfluoroether compounds such as PFOA and hexafluoropropylene oxide dimer acid (GenX) underwent near-complete photodegradation and effective defluorination by continuously generating •H through perfluoroalkyl radical activation of water under UV irradiation without any reagents and catalysts.
View Article and Find Full Text PDFPractical considerations for the optimization of in situ mineralization of perfluorocarboxylic acids and polyfluoroalkyl substances using persulfate oxidation.
Water Res
December 2024
Department of Civil and Environmental Engineering, University of California, Berkeley, CA, 94720, United States. Electronic address:
Military bases and airports are often contaminated by per- and polyfluoroalkyl substances (PFAS) due to the repeated use of aqueous film forming foams (AFFFs) from decades of training exercises, equipment testing, and extinguishing of fuel- and solvent-based fires. Pump-and-treat systems combined with sorption processes are common ex situ remediation strategies; however, they can be expensive and may require decades of operation, particularly at sites where long-term diffusion and desorption of contaminants are the primary release processes. Alternatively, in situ chemical oxidation is an effective remediation strategy in which oxidants (e.
View Article and Find Full Text PDFDefluorinative Cyclization of Enamides with Fluoroalkyl Halides Through Two Vicinal C(sp)─F Bonds Functionalization.
Adv Sci (Weinh)
December 2024
Technical Institute of Fluorochemistry, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, 211816, China.
Introducing distinctive functional groups to expand the structural diversity and improve the intrinsic properties of parent molecules has been an essential pursuit in organic chemistry. By using perfluoroalkyl halide (PFAH) as a nontraditional, readily available, ideal 1,2-difluoroalkenyl coupling partner, a defluorinative cyclization reaction of enamides for the construction of fluoroalkenyl oxazoles is first developed. The selective and controllable two-fold cleavage of vicinal C(sp)─F bonds in PFAH not only enables the introduction of a specific 1,2-difluoroalkenyl moiety with ease but also results in the functionalization of two C(sp)─H bonds of enamides without the need for metal catalyst, photocatalyst, oxidant, or light.
View Article and Find Full Text PDFAssociation Kinetics for Perfluorinated -Alkyl Radicals.
J Phys Chem A
January 2025
Chemical Sciences and Engineering Division, Argonne National Laboratory, Lemont, Illinois 60439, United States.
Radical-radical reaction channels are important in the pyrolysis and oxidation chemistry of perfluoroalkyl substances (PFAS). In particular, unimolecular dissociation reactions within unbranched -perfluoroalkyl chains, and their corresponding reverse barrierless association reactions, are expected to be significant contributors to the gas-phase thermal decomposition of families of species such as perfluorinated carboxylic acids and perfluorinated sulfonic acids. Unfortunately, experimental data for these reactions are scarce and uncertain.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!