Ammonium Salts as Convenient Radical Precursors Using Iridium Photoredox Catalysis

Ammonium salts are usually considered as highly challenging to reduce into the corresponding radicals because of the strength of their carbon-nitrogen bond. Here, we disclose that several ammonium salts can be readily activated using iridium photoredox catalysis to form radicals and illustrate the synthetic utility of this activation of strong C-N bonds with hydrodeamination reactions and radical couplings. Cyclic voltammetry was exploited to rationalize the reactivity observed for the activation of these ammonium salts.

Automated summary

We disclose that ammonium salts can be readily activated using iridium photoredox catalysis to form radicals, and demonstrate the synthetic utility of this activation with hydrodeamination reactions and radical couplings. Cyclic voltammetry was used to rationalize the reactivity observed for the activation of these ammonium salts.