Visible-Light-Promoted Site-Specific and Diverse Functionalization of a C(sp3)-C(sp3) Bond Adjacent to an Arene

We report here a strategy for inert C-C bond functionalization. Site-specific cleavage and functionalization of a saturated C(sp(3))-C(sp(3)) bond via a visible-light-induced radical process have been achieved. The general features of this reaction are as follows. (1) Both linear and cyclic C(sp(3))-C(sp(3)) bonds with a vicinal arene can be specifically functionalized. (2) One carbon is converted into a ketone, and another can be tunably converted into nitrile, peroxide, or halide. (3) The typical conditions include 1.0 mol % of Ru(bpy)(3)Cl-2, 1.0 or 5.0 equiv of Zhdankin reagent, white CFL (24 W), open flask, and room temperature. These reactions offer powerful tools to modify carbon skeletons that are intractable by conventional methods. Good selectivity and functional group tolerance, together with mild and open air conditions, make these transformations valuable and attractive.