Visible-Light-Promoted Aryl Cation Formation: Aromatic SN1 Reactions of Areneazo-2-(2-nitro)propanes

The visible light excitation of areneazo-2-(2-nitro)-propane center dot HCl salts generated the singlet aryl cation that readily underwent aromatic S(N)1 reactions with a variety of nucleophiles. The in situ generated singlet aryl cation was stabilized by a counter nitronate anion that prevented other intersystem crossing and single electron transfer processes. With the improved safety features of neutral areneazo-2-(2-nitro)propane derivatives, the current visiblelight-promoted aromatic S(N)1 reactions provide an alternative aryl C-sp(2)-X bond forming strategy.

Automated summary

The visible light excitation of areneazo-2-(2-nitro)-propane center dot HCl salts generated singlet aryl cation that underwent aromatic S(N)1 reactions with various nucleophiles. The stabilization of the in situ generated singlet aryl cation by a counter nitronate anion prevented other intersystem crossing and single electron transfer processes. With improved safety features, the current visible light-promoted reactions provide an alternative strategy for aryl C-sp(2)-X bond formation.