Aromatic nitration has tremendous importance in organic chemistry as nitroaromatic compounds serve as versatile building blocks. This study represents the electrochemical aromatic nitration with NBu NO , which serves a dual role as supporting electrolyte and as a safe, readily available, and easy-to-handle nitro source. Stoichiometric amounts of 1,1,1-3,3,3-hexafluoroisopropan-2-ol (HFIP) in MeCN significantly increase the yield by solvent control. The reaction mechanism is based on electrochemical oxidation of nitrite to NO , which initiates the nitration reaction in a divided electrolysis cell with inexpensive graphite electrodes. Overall, the reaction is demonstrated for 20 examples with yields of up to 88 %. Scalability is demonstrated by a 13-fold scale-up.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9298355 | PMC |
| http://dx.doi.org/10.1002/cssc.202102053 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
DFT investigation of green stabilizer reactions: curcumin in nitrocellulose-based propellants.
J Mol Model
January 2025
Department of Chemistry, Military Institute of Engineering, Praça General Tibúrcio 80, Rio de Janeiro, Brazil.
Context: Nitrocellulose, widely used in energetic materials, is prone to thermal and chemical degradation, compromising safety and performance. Stabilizers are molecules used in the composition of nitrocellulose-based propellants to inhibit the autocatalytic degradation process that produces nitrous gases and free nitric acids. Curcumin, (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, known for its antioxidant properties and a potential green stabilizer, was investigated using Density Functional Theory (DFT) focusing on its interaction with nitrogen dioxide.
View Article and Find Full Text PDFSource attribution, health risk analysis, and policy implications of PAHs and NPAHs in PM[Formula: see text] in Northern Mexico.
Sci Rep
December 2024
Centro de Investigación en Materiales Avanzados S.C. (CIMAV-Mty), Unidad Monterrey, Alianza Norte 202, Apodaca, N.L., C.P. 66628, Mexico.
This research investigates the concentrations, sources, and health risks of polycyclic aromatic hydrocarbons (PAHs) and nitrated PAHs (NPAHs) in particulate matter with an aerodynamic diameter of 10 μm or less (PM[Formula: see text]) from critical urban centers in northern Mexico: Metropolitan Monterrey Area (MMA), Chihuahua (CHI), and Ciudad Juárez (CDJ). Advanced gas chromatography-mass spectrometry (GC-MS and GC-NCI-MS) revealed significant PAHs concentrations, with levels in MMA reaching 108.89 ± 99.
View Article and Find Full Text PDFSelective Arene Photonitration via Iron-Complex β-Homolysis.
JACS Au
December 2024
State Key Laboratory of Fine Chemicals, School of Chemistry, Dalian University of Technology, Dalian 116024, China.
Nitroaromatics, as an important member and source of nitrogen-containing aromatics, is bringing enormous economic benefits in fields of pharmaceuticals, dyes, pesticides, functional materials, fertilizers, and explosives. Nonetheless, the notoriously polluting nitration industry, which suffers from excessive discharge of fumes and waste acids, poor functional group tolerance, and tremendous purification difficulty, renders mild, efficient, and environmentally friendly nitration a formidable challenge. Herein, we develop a visible-light-driven biocompatible arene C-H nitration strategy with good efficiency and regioselectivity, marvelous substrate applicability and functional group tolerance, and wide application in scale-up synthesis, total synthesis, and late-stage functionalization.
View Article and Find Full Text PDFMechanistic insights into carbonate radical-driven reactions: Selectivity and the hydrogen atom abstraction route.
J Hazard Mater
December 2024
Key Laboratory of Eco-Environments in Three Gorges Reservoir Region, Ministry of Education, College of Environment and Ecology, Chongqing University, Chongqing 400045, PR China.
Carbonate radical (CO) is inevitably produced in advanced oxidation processes (AOPs) when addressing real-world aqueous environments, yet it often goes unnoticed due to its relatively lower reactivity. In this study, we emphasized the pivotal role of CO in targeting the elimination of contaminants by contrasting it with conventional reactive oxygen species (ROSs) and assessing the removal of sulfamethazine (SMT). Similar to singlet oxygen (O), CO shows a preference for electron-rich organic compounds.
View Article and Find Full Text PDFEditorial: Spotlight on North America - chemical sciences.
Front Chem
December 2024
Department of Chemistry and Institute of Chemical Biology and Drug Discovery, Stony Brook University, Stony Brook, NY, United States.
Want 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!