Redox Switching of Orthoquinone-Containing Aromatic Compounds with Hydrogen and Oxygen Gas.

Angew Chem Int Ed Engl

Division of Organic Chemistry, Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, 2-39-1, Kurokami, Chuo-ku, Kumamoto, 860-8555, Japan.

Published: June 2016

Unique redox switching of orthoquinone-containing pentacyclic aromatic compounds with molecular hydrogen and oxygen in the presence of a palladium nanoparticle catalyst (SAPd) is disclosed. These molecules were predicted by in silico screening before synthesis. Efficient protocols for the synthesis of orthoquinone-containing aromatic compounds by palladium-mediated homocoupling and the benzoin condensation reaction were developed. Clear switching between orthoquinone and aromatic hydroquinone compounds was observed on the basis of their photoluminescence properties. Furthermore, the twist strain of the orthoquinone moiety could induce dramatic changes in color and emission.

Download full-text PDF

Source
http://dx.doi.org/10.1002/anie.201601906DOI Listing

Publication Analysis

Top Keywords

aromatic compounds
12
redox switching
8
switching orthoquinone-containing
8
orthoquinone-containing aromatic
8
hydrogen oxygen
8
aromatic
4
compounds
4
compounds hydrogen
4
oxygen gas
4
gas unique
4

Similar Publications

The enantiospecific anti-phytopathogenic fungal activity of a new type of coumarin bearing a phenylpropanoid unit at the 3-position was found. ()-3-[1-Methoxy-3-(4-methoxyphenyl)prop-2-yl]coumarin (()-: EC=16.5 µM) was 30 times more effective than the ()-form against the Japanese pear pathotype.

View Article and Find Full Text PDF

Lemongrass (Poaceae) is one of the aromatic plants with strong odors. Traditionally, lemon grass oil has been used for the treatment of many diseases such as gastrointestinal cramps, high blood pressure, high body temperatures, and fatigue, and is also considered an antibacterial and anti-diarrheal agent. Therefore, this study aims to investigate volatile active constituents and a few important biological activities of the volatile oil of lemongrass (Cymbopogon citratus) grown in Oman.

View Article and Find Full Text PDF

Metagenomic analysis of pristine oil sheds new light on the global distribution of microbial genetic repertoire in hydrocarbon-associated ecosystems.

Microlife

January 2025

Environmental Metagenomics, Research Center One Health Ruhr of the University Alliance Ruhr, Faculty of Chemistry, University of Duisburg-Essen, 45141 Essen, Germany.

Oil reservoirs are society's primary source of hydrocarbons. While microbial communities in industrially exploited oil reservoirs have been investigated in the past, pristine microbial communities in untapped oil reservoirs are little explored, as are distribution patterns of respective genetic signatures. Here, we show that a pristine oil sample contains a complex community consisting of bacteria and fungi for the degradation of hydrocarbons.

View Article and Find Full Text PDF

Molecular docking-guided in-depth investigation of the biological activities and phytochemical and mineral profiles of endemic Phlomis capitata.

J Sci Food Agric

January 2025

Bee and Natural Products R&D and P&D Application and Research Center, Bingöl University, Bingöl, Turkey.

Background: Phlomis capitata is an endemic species of flowering aromatic and medicinal plant in the family Lamiaceae, native to regions of the Mediterranean and nearby areas. Understanding the chemical compounds present in P. capitata can reveal potential medicinal properties.

View Article and Find Full Text PDF

The Electrochemical Iodination of Electron-Deficient Arenes.

Angew Chem Int Ed Engl

January 2025

Institut für Chemie, Carl von Ossietzky Universität Oldenburg, Carl-von-Ossietzky-Straße 9-11, 26129, Oldenburg, Germany.

The iodination of electron-deficient arenes and heteroarenes is a long-standing problem in organic synthesis. Herein we describe the electrochemical iodination in nitromethane with BuNI as iodine source and supporting electrolyte under Lewis acid-free conditions in the presence of small amounts of chloride anions. The electrochemically generated reagent could be applied for the iodination of halogenated arenes, aromatic aldehydes, acids, esters, ketones, as well as nitroarenes to afford the products in good to excellent yields.

View Article and Find Full Text PDF

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!