Synthesis 2018; 50(24): 4933-4939
DOI: 10.1055/s-0037-1610651
paper
© Georg Thieme Verlag Stuttgart · New York

Visible-Light-Driven Oxidative Mono- and Dibromination of Benzylic­ sp3 C–H Bonds with Potassium Bromide/Oxone at Room Temperature

Mengdi Zhao
Department of Chemistry, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. of China   Email: luwj@sjtu.edu.cn
,
Meiqi Li
Department of Chemistry, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. of China   Email: luwj@sjtu.edu.cn
,
Department of Chemistry, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. of China   Email: luwj@sjtu.edu.cn
› Author Affiliations
We thank the National Natural Science Foundation of China (Grant No. 21372153) for financial support.
Further Information

Publication History

Received: 12 June 2018

Accepted after revision: 07 July 2018

Publication Date:
15 August 2018 (online)


M.Z. and M.L. contributed equally to this work.

Abstract

Benzylic sp3 C–H bonds have been successfully brominated with potassium bromide by using Oxone as an oxidant in water/dichloromethane under visible light at room temperature. Toluene, ethylbenzene and other alkylbenzenes bearing an electron-withdrawing group, such as Br, Cl, COMe, CO2Et, CO2H, CN or NO2, provide the corresponding benzylic monobromides in good to excellent yields in this reaction. Dibromides can also be produced in the presence of excess potassium bromide in a prolonged reaction time. Control of the illuminance of visible light (~500 lux) is crucial to achieving both high yield and high selectivity in these brominations. Mono- and difluorides can be conveniently prepared through nucleophilic substitutions of the benzylic bromides with potassium fluoride.

Supporting Information

 
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