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Photoredox-catalyzed difunctionalizations of alkenes with O-acyl hydroxylamine derivatives are described. The solvent tunes the outcome of these reactions. Diamidation and oxidative amidation of alkenes can be achieved in CH3CN and DMSO, respectively. A variety of 1,2-diamidates and α-amino ketones bearing many functional groups are prepared using Ir(ppy)3 as the photocatalyst under visible light irradiation.

Radical alkynyltrifluoromethylation of alkenes with actylenic triflones has been achieved. This radical chain reaction is initiated by a catalytic amount of an electron-donor–acceptor complex composed of Togni’s reagent and N-methylmorpholine. This transformation proceeds under exceptionally mild and operationally simple conditions. A variety of alkenes are compatible in this protocol including aliphatic alkenes, vinyl ethers, enecarbamates, styrenes, and even acrylates, providing diverse β- trifluoromethyl alkynes in good to excellent yields.