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

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 H 2 O/CF 3 CH 2 OH at room temperature. Other secondary and primary alkyl sp 3 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 sp 3 C–H bond or the aryl sp 2 C–H bond of toluene.