Photocatalytic Scaffold Hopping of Cyclobutanols to Cyclopentanols via Single-Carbon Insertion into C–C σ-Bonds

Abstract A method for skeletal editing of C–C σ-bonds in strained alicycles via single-carbon insertion is reported. This skeletal editing method for cyclobutanols differs from well-established semipinacol rearrangement pathways, offering an efficient route to cyclopentanols by direct scaffold hopping of cyclobutanols. This transformation proceeds under mild conditions in good yields, expanding the toolkit for single-atom insertion into C–C σ-bonds.

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Publication Details

Journal
Organic Letters
Published
2026-10-14
DOI
https://doi.org/10.1021/acs.orglett.6c04162
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Photocatalytic Scaffold Hopping of Cyclobutanols to Cyclopentanols via Single-Carbon Insertion into C–C σ-Bonds

Peng Zhao, Can Wang, Xuyang Wang, Yongmin Ma
Organic Letters
Radical Photochemical Reactions
article

Photocatalytic Scaffold Hopping of Cyclobutanols to Cyclopentanols via Single-Carbon Insertion into C–C σ-Bonds

Peng Zhao, Can Wang, Xuyang Wang, Yongmin Ma
article en

Abstract

Abstract A method for skeletal editing of C–C σ-bonds in strained alicycles via single-carbon insertion is reported. This skeletal editing method for cyclobutanols differs from well-established semipinacol rearrangement pathways, offering an efficient route to cyclopentanols by direct scaffold hopping of cyclobutanols. This transformation proceeds under mild conditions in good yields, expanding the toolkit for single-atom insertion into C–C σ-bonds.

Organic Letters
Taizhou University (CN), Taizhou University (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 26%
Radical Photochemical Reactions
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