Visible-Light-Driven Photoredox-Catalyzed Radical Cyclization via a TEMPO-Intercepted Cascade: Regioselective and Access to Cyclopentene Skeletons

Qi Jiang; Keyuan Zhang; Mingyou Hu; Xin Hua Duan; Le Liu

doi:10.1021/acs.orglett.5c03155

Visible-Light-Driven Photoredox-Catalyzed Radical Cyclization via a TEMPO-Intercepted Cascade: Regioselective and Access to Cyclopentene Skeletons

Qi Jiang
, Keyuan Zhang
, Mingyou Hu
, Xin Hua Duan
, Le Liu

School of Chemistry

Xi'an Jiaotong University

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

Abstract

A visible-light-driven regioselective intramolecular cyclization and oxidation cascade of γ-alkynyl β-sulfonylester is developed. This metal-free approach efficiently affords synthetically useful cyclopentene and cyclohexene skeletons under mild conditions, with TEMPO acting as a dual electron and oxygen atom donor. Mechanism investigations support a radical cyclization/TEMPO-trapping cascade.

Original language	English
Pages (from-to)	10088-10092
Number of pages	5
Journal	Organic Letters
Volume	27
Issue number	36
DOIs	https://doi.org/10.1021/acs.orglett.5c03155
State	Published - 12 Sep 2025

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title = "Visible-Light-Driven Photoredox-Catalyzed Radical Cyclization via a TEMPO-Intercepted Cascade: Regioselective and Access to Cyclopentene Skeletons",

abstract = "A visible-light-driven regioselective intramolecular cyclization and oxidation cascade of γ-alkynyl β-sulfonylester is developed. This metal-free approach efficiently affords synthetically useful cyclopentene and cyclohexene skeletons under mild conditions, with TEMPO acting as a dual electron and oxygen atom donor. Mechanism investigations support a radical cyclization/TEMPO-trapping cascade.",

author = "Qi Jiang and Keyuan Zhang and Mingyou Hu and Duan, \{Xin Hua\} and Le Liu",

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

year = "2025",

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doi = "10.1021/acs.orglett.5c03155",

language = "英语",

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TY - JOUR

T1 - Visible-Light-Driven Photoredox-Catalyzed Radical Cyclization via a TEMPO-Intercepted Cascade

T2 - Regioselective and Access to Cyclopentene Skeletons

AU - Jiang, Qi

AU - Zhang, Keyuan

AU - Hu, Mingyou

AU - Duan, Xin Hua

AU - Liu, Le

PY - 2025/9/12

Y1 - 2025/9/12

N2 - A visible-light-driven regioselective intramolecular cyclization and oxidation cascade of γ-alkynyl β-sulfonylester is developed. This metal-free approach efficiently affords synthetically useful cyclopentene and cyclohexene skeletons under mild conditions, with TEMPO acting as a dual electron and oxygen atom donor. Mechanism investigations support a radical cyclization/TEMPO-trapping cascade.

AB - A visible-light-driven regioselective intramolecular cyclization and oxidation cascade of γ-alkynyl β-sulfonylester is developed. This metal-free approach efficiently affords synthetically useful cyclopentene and cyclohexene skeletons under mild conditions, with TEMPO acting as a dual electron and oxygen atom donor. Mechanism investigations support a radical cyclization/TEMPO-trapping cascade.

UR - https://www.scopus.com/pages/publications/105015668112

U2 - 10.1021/acs.orglett.5c03155

DO - 10.1021/acs.orglett.5c03155

M3 - 快报

C2 - 40876960

AN - SCOPUS:105015668112

SN - 1523-7060

VL - 27

SP - 10088

EP - 10092

JO - Organic Letters

JF - Organic Letters

IS - 36

ER -

Visible-Light-Driven Photoredox-Catalyzed Radical Cyclization via a TEMPO-Intercepted Cascade: Regioselective and Access to Cyclopentene Skeletons

Abstract

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