Bifunctional Sodium Dithionite Promoted Radical-Polar Crossover Cyclization: Diversified Synthesis of Functionalized Cyclic Sultines

A catalyst-free reductive radical-polar crossover cyclization with alkenes and sodium dithionite to construct densely functionalized cyclic sultines was described. The key to the success of this practical protocol relies not only on a bifunctional role of sodium dithionite, that is, serving as radical initiator and SO<sub>2</sub> source, but also on the diversified conversions (RPCC/SO<sub>2</sub> insertion/S<sub>N</sub>2 cyclization and RPCC/SO<sub>2</sub> insertion/1,4-addition cyclization processes), which enabled efficient construction of target compounds with the high efficiency and atom- and step-economy under mild conditions.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-12-11
DOI
https://doi.org/10.1021/acs.joc.4c02606
Citations
3
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.75

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article

Bifunctional Sodium Dithionite Promoted Radical-Polar Crossover Cyclization: Diversified Synthesis of Functionalized Cyclic Sultines

Zhonglin Wei, Cheng-Jing Li, Wei‐Wei Liao, Mengyu Liu
3 citations
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
0.75
article

Bifunctional Sodium Dithionite Promoted Radical-Polar Crossover Cyclization: Diversified Synthesis of Functionalized Cyclic Sultines

Zhonglin Wei, Cheng-Jing Li, Wei‐Wei Liao, Mengyu Liu
article en
3 citations

Abstract

A catalyst-free reductive radical-polar crossover cyclization with alkenes and sodium dithionite to construct densely functionalized cyclic sultines was described. The key to the success of this practical protocol relies not only on a bifunctional role of sodium dithionite, that is, serving as radical initiator and SO<sub>2</sub> source, but also on the diversified conversions (RPCC/SO<sub>2</sub> insertion/S<sub>N</sub>2 cyclization and RPCC/SO<sub>2</sub> insertion/1,4-addition cyclization processes), which enabled efficient construction of target compounds with the high efficiency and atom- and step-economy under mild conditions.

The Journal of Organic ChemistryVol. 89(24)
Jilin University (CN), Chinese Academy of Sciences (CN), Shanghai Institute of Organic Chemistry (CN)
State Key Laboratory of Supramolecular Structure and Materials, National Key Research and Development Program of China
Openalex Percentile: Top 31%
Sulfur-Based Synthesis Techniques
0.75
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