R <sub>3</sub> P/ICH <sub>2</sub> CH <sub>2</sub> I-Promoted Skeletal Editing of Cyclic Ethers via O/N Exchange

The functionalization of cyclic ethers has received significant attention; however, the skeletal editing of cyclic ethers via O-to-N exchange remains challenging. Herein, we report a R<sub>3</sub>P/ICH<sub>2</sub>CH<sub>2</sub>I-promoted O-to-N exchange of cyclic ethers. This strategy enables the direct conversion of widely available cyclic ethers─such as tetrahydrofuran and 1,4-dioxane─into nitrogen-containing heterocycles, structural motifs commonly found in biologically active molecules. The method exhibits broad compatibility with secondary and tertiary amines, delivering the corresponding products in moderate to good yields.

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Publication Details

Journal
Organic Letters
Published
2026-02-15
DOI
https://doi.org/10.1021/acs.orglett.6c00258
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

R 3 P/ICH 2 CH 2 I-Promoted Skeletal Editing of Cyclic Ethers via O/N Exchange

Jin‐Hong Lin, Yue Zhang, Ji-Chang Xiao
Organic Letters
Catalytic C–H Functionalization Methods
article

R 3 P/ICH 2 CH 2 I-Promoted Skeletal Editing of Cyclic Ethers via O/N Exchange

Jin‐Hong Lin, Yue Zhang, Ji-Chang Xiao
article en

Abstract

The functionalization of cyclic ethers has received significant attention; however, the skeletal editing of cyclic ethers via O-to-N exchange remains challenging. Herein, we report a R<sub>3</sub>P/ICH<sub>2</sub>CH<sub>2</sub>I-promoted O-to-N exchange of cyclic ethers. This strategy enables the direct conversion of widely available cyclic ethers─such as tetrahydrofuran and 1,4-dioxane─into nitrogen-containing heterocycles, structural motifs commonly found in biologically active molecules. The method exhibits broad compatibility with secondary and tertiary amines, delivering the corresponding products in moderate to good yields.

Organic LettersVol. 28(8)
Shanghai University (CN), Shanghai Institute of Organic Chemistry (CN), Innovative Research (United States) (US), University of Chinese Academy of Sciences (CN)
Openalex Percentile: Top 53%
Catalytic C–H Functionalization Methods
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