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Paper | Special issue | Vol 103, No. 2, 2021, pp.878-892
Published online, 22nd February, 2021
DOI: 10.3987/COM-20-S(K)54
Polyfluoroarene-Capped Thiophene Derivatives via Fluoride-Catalyzed Nucleophilic Aromatic Substitution

Kotaro Kikushima, Kana Matsuki, Yuna Yoneda, Takayuki Menjo, Kosuke Kaneko, Tomonori Hanasaki, and Toshifumi Dohi*

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


Arylthiophene derivatives are potential components of functional materials, including organic electronics. Herein, we describe a nucleophilic aromatic substitution reaction of polyfluoroarenes using silylthiophenes as nucleophiles in the presence of a catalytic amount of a fluoride salt. Various polyfluoroarene-capped thiophene derivatives were synthesized via double arylation under transition metal-free conditions. A fluoride ion activates a silylthiophene to trigger a nucleophilic aromatic substitution, subsequently affording the coupling product along with elimination of the fluoride ion, which serves as a promoter of the catalytic reaction.