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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Electrochemically chalcogenative annulation enabled construction of functionalized saturated N-heterocycles
Jian Wang1, Xinxin Zhao1, Yijia Wang1
1School of Chemistry and Pharmacy Engineering, Nanyang Normal University, Nanyang, 473061, China. 20222044@nynu.edu.cn.
This study introduces an electrochemical method for creating functionalized N-heterocycles from alkenes and dichalcogenides. The efficient strategy yields various saturated nitrogen heterocycles with high regioselectivity.
Area of Science:
- Organic Chemistry
- Electrochemistry
- Synthetic Methodology
Background:
- N-heterocycles are crucial structural motifs in pharmaceuticals and natural products.
- Developing efficient synthetic routes to functionalized N-heterocycles remains a significant challenge in organic synthesis.
Purpose of the Study:
- To present a novel electrochemical chalcogenative annulation strategy for synthesizing saturated N-heterocycles.
- To demonstrate the applicability of this method to various alkene substrates and its potential for oxychalcogenation.
Main Methods:
- Electrochemical synthesis utilizing dichalcogenides and unactivated alkenes.
- Exploration of reaction scope with mono-, di-, and tri-substituted alkenes.
- Analysis of regioselectivity in the formation of heterocyclic products.
Main Results:
- Successful construction of functionalized saturated N-heterocycles, including aziridines, azetidines, pyrrolidines, and piperidines.
- High regioselectivity observed in the annulation reactions.
- Demonstration of the protocol's capability for concurrent oxychalcogenation of alkenes.
Conclusions:
- The developed electrochemical strategy offers an efficient and versatile pathway for synthesizing diverse N-heterocycles.
- This method provides a valuable tool for accessing complex nitrogen-containing compounds with controlled stereochemistry.
- The protocol's applicability to unactivated alkenes expands its synthetic utility.
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