Visible-Light-Promoted Aryl Cation Formation: Aromatic SN1 Reactions of Areneazo-2-(2-nitro)propanes
Dilip V Patil1, Karu Ramesh1, Hun Young Kim2
1Center for Metareceptome Research, Graduate School of Pharmaceutical Sciences, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul 06974, Republic of Korea.
Abstract:
The visible light excitation of areneazo-2-(2-nitro)propane·HCl salts generated the singlet aryl cation that readily underwent aromatic SN1 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 visible-light-promoted aromatic SN1 reactions provide an alternative aryl Csp2-X bond forming strategy.
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