Synthesis of 2-Organoselenyl Quinolines via Electro-Oxidative Selenocyclization of Isocyanides

Organoselenium compounds and quinolines are widely used in drugs and materials. Herein, we report an electro-oxidative cyclization between isocyanides and diselenides to effectively synthesize 2-organoselenyl quinolines in a simple undivided cell without transition-metal catalysts or toxic oxidants. Gram-scale synthesis and postsynthetic modifications highlighted the practicality of this electrochemical strategy. A series of 2-organoselenyl quinolines are produced with up to 82% yield, good functional group tolerance and high atom efficiency under room temperature.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-03-12
DOI
https://doi.org/10.1021/acs.joc.5c00087
Citations
9
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
8.42

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article

Synthesis of 2-Organoselenyl Quinolines via Electro-Oxidative Selenocyclization of Isocyanides

Kewen Tang, Peng‐Fei Huang, Jia-Le Fu, Yu Liu et al.
9 citations
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
8.42
article

Synthesis of 2-Organoselenyl Quinolines via Electro-Oxidative Selenocyclization of Isocyanides

Kewen Tang, Peng‐Fei Huang, Jia-Le Fu, Yu Liu, Zhi-Gang Quan
article en
9 citations

Abstract

Organoselenium compounds and quinolines are widely used in drugs and materials. Herein, we report an electro-oxidative cyclization between isocyanides and diselenides to effectively synthesize 2-organoselenyl quinolines in a simple undivided cell without transition-metal catalysts or toxic oxidants. Gram-scale synthesis and postsynthetic modifications highlighted the practicality of this electrochemical strategy. A series of 2-organoselenyl quinolines are produced with up to 82% yield, good functional group tolerance and high atom efficiency under room temperature.

The Journal of Organic ChemistryVol. 90(11)
Hunan Institute of Science and Technology (CN)
National Natural Science Foundation of China, Natural Science Foundation of Hunan Province
Openalex Percentile: Top 2%
Sulfur-Based Synthesis Techniques
8.42
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