Sulfinate-Promoted Defluorinative Cyclization of Polyfluoroalkyl Tetralones Enabled by Photocatalysis

Ming Yao Tang; Xiao Ying Li; Xiao Xiao Sun; Hao Xu; Mengtao Ma; Zhi Liang Shen; Xue Qiang Chu

doi:10.1021/acs.orglett.5c00214

Sulfinate-Promoted Defluorinative Cyclization of Polyfluoroalkyl Tetralones Enabled by Photocatalysis

Ming Yao Tang, Xiao Ying Li, Xiao Xiao Sun, Hao Xu, Mengtao Ma, Zhi Liang Shen, Xue Qiang Chu

School of Chemistry and Moleculai Engineering

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

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(sp³)-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.

Original language	English
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.5c00214
State	Accepted/In press - 2025

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10.1021/acs.orglett.5c00214

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title = "Sulfinate-Promoted Defluorinative Cyclization of Polyfluoroalkyl Tetralones Enabled by Photocatalysis",

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(sp3)-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.",

author = "Tang, {Ming Yao} and Li, {Xiao Ying} and Sun, {Xiao Xiao} and Hao Xu and Mengtao Ma and Shen, {Zhi Liang} and Chu, {Xue Qiang}",

note = "Publisher Copyright: {\textcopyright} 2025 American Chemical Society.",

year = "2025",

doi = "10.1021/acs.orglett.5c00214",

language = "英语",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Sulfinate-Promoted Defluorinative Cyclization of Polyfluoroalkyl Tetralones Enabled by Photocatalysis

AU - Tang, Ming Yao

AU - Li, Xiao Ying

AU - Sun, Xiao Xiao

AU - Xu, Hao

AU - Ma, Mengtao

AU - Shen, Zhi Liang

AU - Chu, Xue Qiang

PY - 2025

Y1 - 2025

N2 - 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(sp3)-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.

AB - 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(sp3)-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.

UR - http://www.scopus.com/inward/record.url?scp=85216879479&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.5c00214

DO - 10.1021/acs.orglett.5c00214

M3 - 文章

AN - SCOPUS:85216879479

SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

ER -

Sulfinate-Promoted Defluorinative Cyclization of Polyfluoroalkyl Tetralones Enabled by Photocatalysis

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