Sulfinate-PromotedDefluorinative Cyclization of PolyfluoroalkylTetralones Enabled by Photocatalysis

A Ru-catalyzed defluorinative cyclization of polyfluoroalkyl tetralones has been developed under visible-light irradiation for the precise assembly of γ-pyrones featuring α-perfluoroalkyl and β-fluorine substituents. Selective functionalization of five C(sp<sup>3</sup>)–F bonds at three carbon sites on the perfluoroalkyl chain provides a new mode for utilizing polyfluorides as versatile synthons to access difficult-to-obtain heterocyclic scaffolds. Moreover, the sulfinate salt serves dual roles as an oxygen source for creating the carbonyl group and as a defluorinating promoter.

Publication Details

Journal
Figshare
Published
2025-02-03
DOI
https://doi.org/10.1021/acs.orglett.5c00214.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
Type
article
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article

Sulfinate-PromotedDefluorinative Cyclization of PolyfluoroalkylTetralones Enabled by Photocatalysis

Figshare
Mycorrhizal Fungi and Plant Interactions
article

Sulfinate-PromotedDefluorinative Cyclization of PolyfluoroalkylTetralones Enabled by Photocatalysis

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Abstract

A Ru-catalyzed defluorinative cyclization of polyfluoroalkyl tetralones has been developed under visible-light irradiation for the precise assembly of γ-pyrones featuring α-perfluoroalkyl and β-fluorine substituents. Selective functionalization of five C(sp<sup>3</sup>)–F bonds at three carbon sites on the perfluoroalkyl chain provides a new mode for utilizing polyfluorides as versatile synthons to access difficult-to-obtain heterocyclic scaffolds. Moreover, the sulfinate salt serves dual roles as an oxygen source for creating the carbonyl group and as a defluorinating promoter.

Figshare
Clean water and sanitation
Openalex Percentile: Top 53%
Mycorrhizal Fungi and Plant Interactions
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Sulfinate-PromotedDefluorinative Cyclization of PolyfluoroalkylTetralones Enabled by Photocatalysis · Figshare (2025) | TGRS Research Map | TGRS