Ring-Opening Sulfonylation of Cyclic Sulfonium Salts with Sodium Sulfinates under Transition-Metal- and Additive-Free Conditions

Incorporating a sulfonyl group into parent molecules has been shown to effectively improve their synthetic applications and bioactivities. In this study, we present a straightforward and practical approach for the ring-opening reaction of alkenyl-aryl sulfonium salts with sodium sulfinates to produce a range of sulfur-containing alkyl sulfones. This method offers the benefits of mild reaction conditions, easily accessible raw materials, wide substrate applicability, good functional group compatibility, and operational simplicity. Importantly, the resulting products can be readily converted into sulfoxides, sulfones, sulfoximines, and some heterocyclic compounds.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-08-09
DOI
https://doi.org/10.1021/acs.joc.4c01621
Citations
21
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
5.25

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article

Ring-Opening Sulfonylation of Cyclic Sulfonium Salts with Sodium Sulfinates under Transition-Metal- and Additive-Free Conditions

Long‐Yong Xie, Xiangda Liu Xiangda Liu, Siyu Wang, Chu Liu et al.
21 citations
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
5.25
article

Ring-Opening Sulfonylation of Cyclic Sulfonium Salts with Sodium Sulfinates under Transition-Metal- and Additive-Free Conditions

Long‐Yong Xie, Xiangda Liu Xiangda Liu, Siyu Wang, Chu Liu, Li‐Hua Yang
article en
21 citations

Abstract

Incorporating a sulfonyl group into parent molecules has been shown to effectively improve their synthetic applications and bioactivities. In this study, we present a straightforward and practical approach for the ring-opening reaction of alkenyl-aryl sulfonium salts with sodium sulfinates to produce a range of sulfur-containing alkyl sulfones. This method offers the benefits of mild reaction conditions, easily accessible raw materials, wide substrate applicability, good functional group compatibility, and operational simplicity. Importantly, the resulting products can be readily converted into sulfoxides, sulfones, sulfoximines, and some heterocyclic compounds.

The Journal of Organic ChemistryVol. 89(17)
Hunan University of Science and Engineering (CN)
National Natural Science Foundation of China, Science and Technology Program of Hunan Province
Clean water and sanitation
Openalex Percentile: Top 3%
Sulfur-Based Synthesis Techniques
5.25
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