Alkyl spC-H bonds of cycloalkanes and functional branch/linear alkanes have been successfully brominated with KBr using air or O as an oxidant at room temperature to 40 °C. The reactions are carried out in the presence of catalytic NaNO in 37% HCl (aq)/solvent under visible light, combining aerobic oxidations and photochemical radical processes. For various alkane substrates, CFCHOH, CHCl, or CHCl is employed as an organic solvent, respectively, to enhance the efficiency of bromination.
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 HO/CFCHOH at room temperature. Other secondary and primary alkyl sp 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 C-H bond or the aryl sp C-H bond of toluene.
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