Journal
ORGANIC LETTERS
Volume 25, Issue 39, Pages 7204-7208Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c02783
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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.
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.
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