Visible-Light-Promoted Aryl Cation Formation: Aromatic S_N1 Reactions of Areneazo-2-(2-nitro)propanes

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.

Fine bubble technology for the green synthesis of fairy chemicals

“…We sought an alternative method to increase the yield in less time. 31 Before synthesising AHX from DICA, we found that the previously known intermediate, DICA 5 , was stable at solid state (see ESI†). Therefore, we characterised DICA 5 using NMR and IR spectral data (Scheme 6).…”

Visible photons as ideal reagents for the activation of coloured organic compounds

“…This approach was a good strategy for the formation of C(sp 2 )–X bonds, allowing for the synthesis of compounds 115.4 . 355…”