Direct functionalization of C(sp)-H bonds allows rapid access to valuable products, starting from simple petrochemicals. However, the chemical transformation of non-activated methylene groups remains challenging for organic synthesis. Here, we report a general electrochemical method for the oxidation of C(sp)-H and C(sp)-H bonds, in which cyclic alkanes and (cyclic) olefins are converted into cycloaliphatic ketones as well as aliphatic (di)carboxylic acids. This resource-friendly method is based on nitrate salts in a dual role as anodic mediator and supporting electrolyte, which can be recovered and recycled. Reducing molecular oxygen as a cathodic counter reaction leads to efficient convergent use of both electrode reactions. By avoiding transition metals and chemical oxidizers, this protocol represents a sustainable oxo-functionalization method, leading to a valuable contribution for the sustainable conversion of petrochemical feedstocks into synthetically usable fine chemicals and commodities.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10382549 | PMC |
| http://dx.doi.org/10.1038/s41467-023-40259-0 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
In situ growth of defective ZIF-8 on TEMPO-oxidized cellulose nanofibrils for rapid response release of curcumin in food preservation.
Carbohydr Polym
March 2025
Liaoning Key Lab of Lignocellulose Chemistry and BioMaterials, Liaoning Collaborative Innovation Center for Lignocellulosic Biorefinery, College of Light Industry and Chemical Engineering, Dalian Polytechnic University, Dalian 116034, China. Electronic address:
Uncontrolled release of active agents in active packaging reduces antimicrobial efficacy, hindering the effective protection of perishable products from microbial infection. Herein, a novel defective engineering was proposed to design defective and hollow ZIF-8 structures grown on TEMPO oxidized cellulose nanofibrils (TOCNFs) and use them as fast-reacting nanocarriers for loading and controlled release curcumin (Cur) in sodium alginate (SA) active packaging systems (CZT-Cur-SA). By employing stable chelation between tannic acid (TA) and ZIF-8 zinc ions, the connections between zinc ions and imidazole ligands were severed to form a loose and hollow structure, which facilitates the rapid reaction and release of active ingredients triggered by pH changes in the microenvironment.
View Article and Find Full Text PDFStrong emissions and aerosol formation potential of higher alkanes from diesel vehicles.
J Hazard Mater
December 2024
College of Environment and Climate, Institute for Environmental and Climate Research, Guangdong-Hongkong-Macau Joint Laboratory of Collaborative Innovation for Environmental Quality, Jinan University, 51143, China.
Higher alkanes are a major class of intermediate volatile organic compounds (IVOCs) emitted by vehicles, which have been considered as important precursors of secondary organic aerosol (SOA) in urban area. Dynamometer experiments were conducted to characterize emissions from gasoline and diesel vehicles in China. Three types of higher alkanes, namely acyclic, cyclic, and bicyclic alkanes, were explicitly quantified through the novel proton transfer reaction time-of-flight mass spectrometer with NO ionization (NO PTR-ToF-MS) with time response of 1 second.
View Article and Find Full Text PDFAlkane degradation coupled to Fe(III) reduction mediated by Gram-positive bacteria.
J Hazard Mater
December 2024
State Key Laboratory of Biogeology and Environmental Geology, School of Environmental Studies, China University of Geosciences, Wuhan 430078, China. Electronic address:
Petroleum hydrocarbon contamination, such as n-alkanes, poses a significant global threat to ecosystems and human health. Microbial remediation emerges as a promising strategy for addressing this issue through both aerobic and anaerobic processes. Notably, the majority of anaerobic hydrocarbon degraders identified to date are Gram-negative bacteria.
View Article and Find Full Text PDFSingle-Carbon Insertion into Single C-C Bonds with Diazirines.
J Am Chem Soc
January 2025
Institute of Chemical Research of Catalonia (ICIQ-CERCA), The Barcelona Institute of Science and Technology, Països Catalans 16, 43007 Tarragona, Spain.
A novel platform for the skeletal editing of single C-C bonds via a single-carbon insertion has been developed using diazirines. This strategy involves the photogeneration of arylchlorocarbenes as carbynoid species that undergo site-selective carbene insertion into tertiary C-H bonds and a subsequent Wagner-Meerwein rearrangement promoted by a silver salt. Our skeletal editing strategy based on a formal selective carbyne C-C bond insertion has been demonstrated in six core-to-core conversions, including linear and cyclic benzylic substrates, alkanes and late-stage functionalizations.
View Article and Find Full Text PDFPhotocatalytic CeCl-Promoted C-H Alkenylation and Alkynylation of Alkanes.
Chemistry
December 2024
Laboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, 15771, Panepistimiopolis, Athens, Greece.
The reemerging field of photoredox catalysis offers numerous advantages towards the development of novel, sustainable and easy-to-execute organic transformations. Herein, we report a light-triggered application of cerium complexes towards the C-H alkenylation and alkynylation of alkanes. An indirect HAT-mediated photocatalytic protocol was developed, using a cerium salt (CeCl ⋅ 7HO) and a chlorine source (TBACl) as the catalytic system.
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!