Nucleophilic Aromatic Substitution of Polyfluoroarene to Access Highly Functionalized 10-Phenylphenothiazine Derivatives

Nucleophilic aromatic substitution (SNAr) reactions can provide metal-free access to synthesize monosubstituted aromatic compounds. We developed efficient SNAr conditions for p-selective substitution of polyfluoroarenes with phenothiazine in the presence of a mild base to afford the corresponding 10-phenylphenothiazine (PTH) derivatives. The resulting polyfluoroarene-bearing PTH derivatives were subjected to a second SNAr reaction to generate highly functionalized PTH derivatives with potential applicability as photocatalysts for the reduction of carbon-halogen bonds.

Automated summary

The study demonstrates metal-free synthesis of monosubstituted aromatic compounds via nucleophilic aromatic substitution reactions, resulting in functionalized PTH derivatives through two-step reactions, some of which show potential application as photocatalysts for carbon-halogen bond reduction.