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

Author(s) Sekino, K.; Shida, N.; Shiki, R.; Takigawa, N.; Nishiyama, H.; Tomita, I.; Inagi, S.
Journal Org Lett
Date Published 2020 Feb 25
Abstract

The fluoride-ion-catalyzed synthesis of benzobisbenzofuran derivatives is described. Fluorine-containing aryl silyl ethers were reacted with 5 mol % of BuNF 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.

DOI 10.1021/acs.orglett.0c00531
ISSN 1523-7052
Citation Sekino K, Shida N, Shiki R, Takigawa N, Nishiyama H, Tomita I, et al. Fluoride-Ion-Catalyzed Synthesis of Ladder-type Conjugated Benzobisbenzofurans via Intramolecular Nucleophilic Aromatic Substitution Reaction under Metal-free and Mild Conditions. Org Lett. 2020.

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