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

化学与分子工程学院

科研成果: 期刊稿件 › 文章 › 同行评审

3 引用（Scopus）

摘要

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.

源语言	英语
期刊	Organic Letters
DOI	https://doi.org/10.1021/acs.orglett.5c00214
出版状态	已接受/待刊 - 2025

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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",

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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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