The selective electrochemical fluorination of -alkyl benzothioate and its derivatives.

Beilstein J Org Chem

Department of Electronic Chemistry, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8502, Japan.

Published: February 2018

We herein report that the regioselective anodic fluorination of -alkyl benzothioate and its derivatives in various aprotic solvents using EtN·HF ( = 3-5) and EtNF·HF ( = 3-5) as supporting electrolyte and a fluorine source successfully provided the corresponding α-fluorinated products in moderate yields. Dichloromethane containing EtNF·4HF was found to be the most suitable combination as electrolytic solvent and supporting salt as well as fluorine source for the anodic fluorination. The electrochemical fluorination of cyclic benzothioates such as benzothiophenone was also achieved.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5827776PMC
http://dx.doi.org/10.3762/bjoc.14.27DOI Listing

Publication Analysis

Top Keywords

electrochemical fluorination
8
fluorination -alkyl
8
-alkyl benzothioate
8
benzothioate derivatives
8
anodic fluorination
8
fluorine source
8
selective electrochemical
4
fluorination
4
derivatives report
4
report regioselective
4

Similar Publications

High degree of fluorination for ether electrolytes has resulted in improved cycling stability of lithium metal batteries due to stable solid electrolyte interphase (SEI) formation and good oxidative stability. However, the sluggish ion transport and environmental concerns of high fluorination degree drive the need to develop less fluorinated structures. Here, we depart from the traditional ether backbone and introduce bis(2-fluoroethoxy)methane (F2DEM), featuring monofluorination of the acetal backbone.

View Article and Find Full Text PDF

Spiro architectures with π-conjugation have improved thermal stability and stronger photosensitivity, making them potentially useful for organic optoelectronic devices. Our recent work has demonstrated the synthetic chemistry of a novel thiophene oligomer combining 2,7-dihydrooxepine and dispiro structure and derived it into A-D-A-type compounds. The optical spectroscopy and electrochemical characteristics were investigated.

View Article and Find Full Text PDF

Fluorinated organosilane polycondensation enables a robust Si anode for lithium storage.

Chem Commun (Camb)

January 2025

State Key Lab of Fine Chemicals, Liaoning Key Lab for Energy Materials and Chemical Engineering, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China.

Article Synopsis
  • The chemistry of fluorinated organosilane polycondensation helps create a strong silicon anode coated with a fluorine-doped silicon oxide/carbon composite.
  • Fluorine doping enhances the formation of a coating with less electrochemically active silicon, as well as a lithium fluoride-rich solid electrolyte interphase.
  • This results in a silicon anode that maintains its performance for up to 500 charge cycles at high current densities, making it effective for lithium storage.
View Article and Find Full Text PDF

Water Spillover to Expedite Two-Electron Oxygen Reduction.

Adv Mater

January 2025

Key Laboratory for Soft Chemistry and Functional Materials (Ministry of Education), School of Chemistry and Chemical Engineering, School of Energy and Power Engineering, Nanjing University of Science and Technology, Nanjing, 210094, China.

Limited by the activity-selectivity trade-off relationship, the electrochemical activation of small molecules (like O, N and CO) rapidly diminishes Faradaic efficiencies with elevated current densities (particularly at ampere levels). Nevertheless, some catalysts can circumvent this restriction in a two-electron oxygen reduction reaction (2e ORR), a sustainable pathway for activating O to hydrogen peroxide (HO). Here we report 2e ORR expedited in a fluorine-bridged copper metal-organic framework catalyst, arising from the water spillover effect.

View Article and Find Full Text PDF

Electrochemical destruction of PFAS at low oxidation potential enabled by CeO electrodes utilizing adsorption and activation strategies.

J Hazard Mater

December 2024

School of Environmental Science and Engineering, Southern University of Science and Technology, Shenzhen 518055, PR China; Guangdong Provincial Key Laboratory of Soil and Groundwater Pollution Control, Southern University of Science and Technology, Shenzhen 518055, PR China. Electronic address:

The persistence and ecological impact of per- and poly-fluoroalkyl substances (PFAS) in water sources necessitate effective and energy-efficient treatment solutions. This study introduces a novel approach using cerium dioxide (CeO) electrodes enhanced with oxygen vacancy (O) to catalyze the defluorination of PFAS. By leveraging the unique affinity between cerium and fluorine-containing species, our approach enables adsorptive preconcentration and catalytic degradation at low oxidation potentials (1.

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!