Polyfluoroarene-capped thiophene derivatives via fluoride-catalyzed nucleophilic aromatic substitution was written by Kikushima, Kotaro;Matsuki, Kana;Yoneda, Yuna;Menjo, Takayuki;Kaneko, Kosuke;Hanasaki, Tomonori;Dohi, Toshifumi. And the article was included in Heterocycles in 2021.Electric Literature of C5F5N The following contents are mentioned in the article:
Herein, a nucleophilic aromatic substitution reaction of polyfluoroarenes using silylthiophenes as nucleophiles was described for the synthesis of polyfluoroarene-capped thiophene derivatives, e.g., I 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. This study involved multiple reactions and reactants, such as 2,3,4,5,6-Perfluoropyridine (cas: 700-16-3Electric Literature of C5F5N).
2,3,4,5,6-Perfluoropyridine (cas: 700-16-3) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the 蟺-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the 蟽 bonds. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Electric Literature of C5F5N