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

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.