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Fluoride-Ion-Catalyzed Synthesis of Ladder-type Conjugated Benzobisbenzofurans via Intramolecular Nucleophilic Aromatic Substitution Reaction under Metal-free and Mild Conditions

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journal contribution
posted on 2020-02-25, 18:35 authored by Katsutoshi Sekino, Naoki Shida, Ryosuke Shiki, Natsuki Takigawa, Hiroki Nishiyama, Ikuyoshi Tomita, Shinsuke Inagi
The fluoride-ion-catalyzed synthesis of benzobisbenzofuran derivatives is described. Fluorine-containing aryl silyl ethers were reacted with 5 mol % of Bu4NF to give desired compounds in high yield under mild conditions. Syn-selective cyclization reaction was discovered for a particular compound as a kinetic product. Computational analysis revealed that the fluorine substituents in the anti-type benzobisbenzofurans affect the order of the molecular orbitals.

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