Journal
MOLECULES
Volume 26, Issue 5, Pages -Publisher
MDPI
DOI: 10.3390/molecules26051365
Keywords
polyfluoroarene; phenothiazine; nucleophilic aromatic substitution; amination; photocatalyst
Funding
- JSPS KAKENHI [18H02014, 19K05466]
- Ritsumeikan Global Innovation Research Organization (R-GIRO)
- Grants-in-Aid for Scientific Research [19K05466, 18H02014] Funding Source: KAKEN
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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.
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.
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