Dehydrogenative Aminooxygenation of Cyclopropylamides Enabled by Cooperative Electrocatalysis

Abstract Herein, we report an unprecedented, sustainable, and atom-economic electrochemical [3 + 3] annulation of cyclopropylamides. Readily accessible amides, carbamates, and ureas serve as dual N/O-functional precursors to precisely steer reaction regiochemistry. This protocol allows straightforward assembly of structurally diversified 1,3-oxazines with exclusive regiocontrol under mild conditions. The developed strategy features excellent functional group tolerance, broad substrate scope, and good scalability at higher reaction concentrations and is also applicable to the late-stage modification of bioactive molecules. Mechanistic studies support a distinctive pathway mediated by synergistic ferrocene/iodide dual catalysis.

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Publication Details

Journal
Organic Letters
Published
2026-10-09
DOI
https://doi.org/10.1021/acs.orglett.6c03749
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
0.00
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article

Dehydrogenative Aminooxygenation of Cyclopropylamides Enabled by Cooperative Electrocatalysis

Ruxue Zhou, Haolin Jiang, 陈 修安, Ming Chen et al.
Organic Letters
Cyclopropane Reaction Mechanisms
article

Dehydrogenative Aminooxygenation of Cyclopropylamides Enabled by Cooperative Electrocatalysis

Ruxue Zhou, Haolin Jiang, 陈 修安, Ming Chen, Wenda Li, Yanjie Fu, Xinxin Zhao, Ting Li, Tiantian Zheng
article en

Abstract

Abstract Herein, we report an unprecedented, sustainable, and atom-economic electrochemical [3 + 3] annulation of cyclopropylamides. Readily accessible amides, carbamates, and ureas serve as dual N/O-functional precursors to precisely steer reaction regiochemistry. This protocol allows straightforward assembly of structurally diversified 1,3-oxazines with exclusive regiocontrol under mild conditions. The developed strategy features excellent functional group tolerance, broad substrate scope, and good scalability at higher reaction concentrations and is also applicable to the late-stage modification of bioactive molecules. Mechanistic studies support a distinctive pathway mediated by synergistic ferrocene/iodide dual catalysis.

Organic Letters
Nanyang Normal University (CN)
Openalex Percentile: Top 24%
Cyclopropane Reaction Mechanisms
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