Shouxin Liu
Highly selective halogenation of unactivated C(sp3)–H with NaX under co-catalysis of visible light and Ag@AgX
Liu, Shouxin; Zhang, Qi; Tian, Xia; Fan, Shiming; Huang, Jing; Whiting, Andrew
Authors
Qi Zhang
Xia Tian
Shiming Fan
Jing Huang
Andrew Whiting andy.whiting@durham.ac.uk
Emeritus Professor
Abstract
The direct selective halogenation of unactivated C(sp3)–H bonds into C-halogen bonds was achieved using a nano Ag/AgCl catalyst at RT under visible light or LED irradiation in the presence of an aqueous solution of NaX/HX as a halide source, in air. The halogenation of hydrocarbons provided mono-halide substituted products with 95% selectivity and yields higher than 90%, with the chlorination of toluene being 81%, far higher than the 40% conversion using dichlorine. Mechanistic studies demonstrated that the reaction is a free radical process using blue light (450–500 nm), with visible light being the most effective light source. Irradiation is proposed to cause AgCl bonding electrons to become excited and electron transfer from chloride ions induces chlorine radical formation which drives the substitution reaction. The reaction provides a potentially valuable method for the direct chlorination of saturated hydrocarbons.
Citation
Liu, S., Zhang, Q., Tian, X., Fan, S., Huang, J., & Whiting, A. (2018). Highly selective halogenation of unactivated C(sp3)–H with NaX under co-catalysis of visible light and Ag@AgX. Green Chemistry, 20(20), 4729-4737. https://doi.org/10.1039/c8gc02628a
Journal Article Type | Article |
---|---|
Acceptance Date | Sep 17, 2018 |
Online Publication Date | Sep 18, 2018 |
Publication Date | Sep 18, 2018 |
Deposit Date | Sep 19, 2018 |
Publicly Available Date | Sep 17, 2019 |
Journal | Green Chemistry |
Print ISSN | 1463-9262 |
Electronic ISSN | 1463-9270 |
Publisher | Royal Society of Chemistry |
Peer Reviewed | Peer Reviewed |
Volume | 20 |
Issue | 20 |
Pages | 4729-4737 |
DOI | https://doi.org/10.1039/c8gc02628a |
Public URL | https://durham-repository.worktribe.com/output/1348852 |
Files
Accepted Journal Article
(920 Kb)
PDF
You might also like
Downloadable Citations
About Durham Research Online (DRO)
Administrator e-mail: dro.admin@durham.ac.uk
This application uses the following open-source libraries:
SheetJS Community Edition
Apache License Version 2.0 (http://www.apache.org/licenses/)
PDF.js
Apache License Version 2.0 (http://www.apache.org/licenses/)
Font Awesome
SIL OFL 1.1 (http://scripts.sil.org/OFL)
MIT License (http://opensource.org/licenses/mit-license.html)
CC BY 3.0 ( http://creativecommons.org/licenses/by/3.0/)
Powered by Worktribe © 2025
Advanced Search