Catalytic Intramolecular Cyclization of Alkynyl Cyclic Acetals via Chemoselective Activation Leading to a Phenanthrene Core

An intramolecular cyclization reaction of alkynyl cyclic acetals to synthesize various phenanthrene derivatives in the presence of silver triflate (AgOTf) or boron trifluoride etherate (BF3·OEt2) as catalysts has been developed. By using AgOTf or BF3·OEt2 appropriately depending on the substituents...

Full description

Saved in:
Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan 2022-05, Vol.95 (5), p.735-742
Main Authors: Yamada, Tsuyoshi, Fujii, Akiko, Park, Kwihwan, Furugen, Chikara, Takagi, Akira, Ikawa, Takashi, Sajiki, Hironao
Format: Article
Language:English
Subjects:
Acetals
Alkynes
Density functional theory
Phenanthrene
Reaction mechanisms
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An intramolecular cyclization reaction of alkynyl cyclic acetals to synthesize various phenanthrene derivatives in the presence of silver triflate (AgOTf) or boron trifluoride etherate (BF3·OEt2) as catalysts has been developed. By using AgOTf or BF3·OEt2 appropriately depending on the substituents various alkynyl cyclic acetals were converted to the corresponding phenanthrene derivatives. Investigations of reaction mechanisms, X-ray structure of the product, and computational density functional theory (DFT) study suggested that the reaction proceeds via alkyne activation (π-activation) or acetal activation (σ-activation) pathways based on π- or σ-Lewis acidities.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.20220036