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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

Highly selective halogenation of unactivated C(sp3)–H with NaX under co-catalysis of visible light and Ag@AgX Thumbnail


Authors

Shouxin Liu

Qi Zhang

Xia Tian

Shiming Fan

Jing Huang



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

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