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

Kotaro Kikushima; Haruka Koyama; Kazuki Kodama; Toshifumi Dohi

doi:10.3390/molecules26051365

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

Molecules. 2021 Mar 4;26(5):1365. doi: 10.3390/molecules26051365.

Authors

Kotaro Kikushima¹, Haruka Koyama¹, Kazuki Kodama¹, Toshifumi Dohi¹

Affiliation

¹ College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan.

Abstract

Nucleophilic aromatic substitution (S_NAr) reactions can provide metal-free access to synthesize monosubstituted aromatic compounds. We developed efficient S_NAr 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 S_NAr reaction to generate highly functionalized PTH derivatives with potential applicability as photocatalysts for the reduction of carbon-halogen bonds.

Keywords: amination; nucleophilic aromatic substitution; phenothiazine; photocatalyst; polyfluoroarene.

MeSH terms

Carbon / chemistry*
Fluorenes / chemistry*
Hydrocarbons, Aromatic / chemistry*
Organic Chemistry Phenomena
Phenothiazines / chemistry*

Substances

Fluorenes
Hydrocarbons, Aromatic
Phenothiazines
Carbon