Photoinduced Disulfide-Catalyzed Intramolecular Anti-Markovnikov Hydroamination through in Situ N-S Species.

Abstract

The photoinduced anti-Markovnikov hydroamination of olefins typically required photocatalysts with a high oxidative ability to initiate the single-electron process. Herein, we alternatively utilize bis(2,4,6-triisopropylphenyl) disulfide, an inexpensive reagent with relatively low oxidative ability, as a photo and hydrogen atom transfer catalyst to achieve intramolecular hydroamination. The mechanistic studies as well as the DFT calculations are consistent with a novel process involving N-centered radical generation through the homolysis of the in situ formed N-S species and subsequent cyclization. An array of diverse nitrogen-containing cycles could be obtained.