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Discovery of Thioxanthone-TfOH Complex as Photoredox Catalyst for Hydrogenation of Alkenes using p-Xylene as both Electron and Hydrogen Sources.

Hydrogenation of alkenes is one of the most fundamental transformations in organic synthesis, which was widely used in petrochemical industry, pharmaceutical industry and food industry. Although numerous hydrogenation methods are developed, novel types of catalysis with new mechanism, and new hydrogen source are still desirable yet exceedingly challenging. Thioxanthone (TX) is widely used in energy transfer photoreactions, but rarely in photoredox process. Here we show catalytic amount of TfOH as cocatalyst can tune TX into a photoredox catalyst with highly enhanced oxidative capability in the hydrogenation of carbonylated alkenes with the cheap petroleum industrial product p -xylene serving as hydrogen source. Deuterium can also be introduced by this method using D 2 O as D source. To the best of our knowledge, this is the first example of using p -xylene as hydrogen source.