Direct difunctionalization of simple alkenes, the incorporation of two functional groups onto a carbon–carbon double bond, is of particular interest to the chemical community owing to its important applications in organic synthesis. Mechanistically, two types of reactions – metal‐catalyzed nucleophilic difunctionalization and radical difunctionalization – dominate this research field. Radical difunctionalization is more appealing from a synthetic perspective than metal‐catalyzed nucleophilic difunctionalization because it allows the conversion of simple alkenes into complex molecules in a rapid and convenient manner. Furthermore, radical difunctionalization allows addition to simple alkenes by various carbon‐centered radicals and even heteroatom‐centered radicals. This review gives an overview of intermolecular and intramolecular radical difunctionalization of simple alkenes, with an emphasis on the reaction patterns and mechanisms, as well as potential applications in synthetic chemistry.

A systematic spectroscopic study of a series of C60 derivatives with different cage functionalizations is reported. The absorption spectra and absorptivities of the derivatives in solution were measured and compared. By recording the fluorescence spectra using a near-infrared-sensitive emission spectrometer (extending to 1200 nm), fluorescence quantum yields of the derivatives were determined quantitatively. Fluorescence lifetimes of the derivatives were obtained using the time-correlated single photon counting technique. The results show that both fluorescence quantum yields and lifetimes are rather similar for the different classes of C60 derivatives. The nonlinear absorptive properties of the derivatives were evaluated by optical limiting measurements in solution and in polymer film using the second harmonic of a Q-switched Nd:Yag laser at 532 nm. Effects of different fullerene cage functionalizations on the photophysical properties and optical limiting responses of the C60 derivatives are discussed.

A novel copper/manganese cocatalyzed direct oxidative coupling of terminal vinylarenes with ketones via C(sp(3))-H bond functionalization following C-C bond formation has been developed using tert-butyl hydroperoxide as the radical initiator. Various ketones underwent a free-radical addition of terminal vinylarenes to give the corresponding 1,4-dicarbonyl products with excellent regioselectivity and efficiency through one step. A possible reaction mechanism has been proposed.