Journal
SYNTHESIS-STUTTGART
Volume 50, Issue 24, Pages 4933-4939Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1610651
Keywords
benzylic C-H bond; bromination; oxidation; photochemistry; room temperature
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Funding
- National Natural Science Foundation of China [21372153]
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Benzylic sp(3) 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 (similar to 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.
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