Photoredox Hydroxy-arylation of the Terminal Double Bond of N-Substituted 3-Methyleneisoindolin-1-ones in Visible Light

Mild and efficient ruthenium-catalyzed hydroxy-arylation of the terminal double bond of N-substituted 3-methyleneisoindolin-1-ones is described. The reaction takes place with aryl diazonium salt as the arylating reagent and water as the hydroxyl source in visible light at ambient temperature. The strategy entails vicinal difunctionalization of alkene and enables construction of 3-benzyl-3-hydroxyisoindolin-1-one heterocyclic scaffolds in moderate to good yields. C-C and C-O bonds are formed in one pot without any external additive and oxidant through an in situ generation of a carbocation intermediate in green light.

Automated summary

A mild and efficient ruthenium-catalyzed hydroxy-arylation reaction of the terminal double bond of N-substituted 3-methyleneisoindolin-1-ones is described in this study. The reaction takes place in the presence of aryl diazonium salt as arylating reagent and water as hydroxyl source under visible light at ambient temperature. This strategy enables the construction of 3-benzyl-3-hydroxyisoindolin-1-one heterocyclic scaffolds through vicinal difunctionalization of the alkene, yielding moderate to good yields. Both C-C and C-O bonds are formed in one pot without the need for external additives or oxidants, through the in situ generation of a carbocation intermediate under green light.