ol0c00531_si_001.pdf (5.47 MB)
Fluoride-Ion-Catalyzed Synthesis of Ladder-type Conjugated Benzobisbenzofurans via Intramolecular Nucleophilic Aromatic Substitution Reaction under Metal-free and Mild Conditions
journal contribution
posted on 2020-02-25, 18:35 authored by Katsutoshi Sekino, Naoki Shida, Ryosuke Shiki, Natsuki Takigawa, Hiroki Nishiyama, Ikuyoshi Tomita, Shinsuke InagiThe 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.
History
Usage metrics
Categories
Keywords
Intramolecular Nucleophilic Aromatic Substitution Reactioncompoundfluoride-ion-catalyzed synthesisorbitalFluorine-containing aryl silyl ethersanti-type benzobisbenzofuransBu 4 NFbenzobisbenzofuran derivativesMild ConditionsMetal-freefluorine substituentsFluoride-Ion-Catalyzed SynthesisSyn-selective cyclization reactionComputational analysisLadder-type Conjugated Benzobisbenzofurans
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC