Visible Light-Mediated [3 + 2] Cycloadditions of Vinylcyclopropanes with Alkenes/Alkynes Using CBr <sub>4</sub> and an Organic Photocatalyst

Utilizing a readily available and highly efficient organic photocatalyst (QXPT-NPy, 0.5 mol %) and inexpensive CBr<sub>4</sub> (0.5 mol %) as a bromine radical precursor, the [3 + 2] cycloadditions of vinylcyclopropanes with alkenes/alkynes were successfully achieved under irradiation of 420 nm blue LEDs. A broad scope of alkenes and alkynes participated efficiently in the reaction, and structurally diverse cyclopentane and cyclopentene derivatives were afforded in up to 97% yield and 95:5 dr.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-02-03
DOI
https://doi.org/10.1021/acs.joc.5c02490
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Visible Light-Mediated [3 + 2] Cycloadditions of Vinylcyclopropanes with Alkenes/Alkynes Using CBr 4 and an Organic Photocatalyst

ZhongWen Wang, Jun Ren, Yanting Yang, Yi Sun et al.
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Visible Light-Mediated [3 + 2] Cycloadditions of Vinylcyclopropanes with Alkenes/Alkynes Using CBr 4 and an Organic Photocatalyst

ZhongWen Wang, Jun Ren, Yanting Yang, Yi Sun, Lin Yuan, Qiang Bian
article en

Abstract

Utilizing a readily available and highly efficient organic photocatalyst (QXPT-NPy, 0.5 mol %) and inexpensive CBr<sub>4</sub> (0.5 mol %) as a bromine radical precursor, the [3 + 2] cycloadditions of vinylcyclopropanes with alkenes/alkynes were successfully achieved under irradiation of 420 nm blue LEDs. A broad scope of alkenes and alkynes participated efficiently in the reaction, and structurally diverse cyclopentane and cyclopentene derivatives were afforded in up to 97% yield and 95:5 dr.

The Journal of Organic ChemistryVol. 91(6)
Nankai University (CN)
Openalex Percentile: Top 67%
Radical Photochemical Reactions
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