Organic Letters
Organic Letters
5 years ago

Visible Light-Induced Oxidative Chlorination of Alkyl sp3 C–H Bonds with NaCl/Oxone at Room Temperature

Visible Light-Induced Oxidative Chlorination of Alkyl sp3 C–H Bonds with NaCl/Oxone at Room Temperature
Mengdi Zhao, Wenjun Lu
A visible light-induced monochlorination of cyclohexane with sodium chloride (5:1) has been successfully accomplished to afford chlorocyclohexane in excellent yield by using Oxone as the oxidant in H2O/CF3CH2OH at room temperature. Other secondary and primary alkyl sp3 C–H bonds of cycloalkanes and functional branch/linear alkanes can also be chlorinated, respectively, under similar conditions. The selection of a suitable organic solvent is crucial in these efficient radical chlorinations of alkanes in two-phase solutions. It is studied further by the achievement of high chemoselectivity in the chlorination of the benzyl sp3 C–H bond or the aryl sp2 C–H bond of toluene.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02153

DOI: 10.1021/acs.orglett.7b02153

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