Visible Light-Induced Oxidative Chlorination of Alkyl sp 3 C-H Bonds with NaCl/Oxone at Room Temperature

Org Lett. 2017 Sep 1;19(17):4560-4563. doi: 10.1021/acs.orglett.7b02153. Epub 2017 Aug 17.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't