β-Thioamide Sulfone Enabled Copper-Catalyzed Ring-Opening/Sulfonylation of Cyclopropenes: Access to Alkyl Aryl Sulfones

Sulfone motifs play important roles in bioactive compounds and functional materials. The development of efficient methodologies for constructing sulfonyl-containing compounds has thus attracted considerable attention. Here, we introduce a protocol for the preparation of alkyl aryl sulfones under mild conditions. This protocol employs β-thioamide sulfone as a novel sulfone motif donor. It forms sulfinates in situ under basic conditions, which then undergo cross-coupling with the intermediates that were generated from ligand-free copper-catalyzed cyclopropenes (CPEs) ring opening.

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Publication Details

Journal
Organic Letters
Published
2025-01-09
DOI
https://doi.org/10.1021/acs.orglett.4c04352
Citations
4
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
3.74

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article

β-Thioamide Sulfone Enabled Copper-Catalyzed Ring-Opening/Sulfonylation of Cyclopropenes: Access to Alkyl Aryl Sulfones

Yi Kong, C.‐S. CHUNG, Qin Yin, Yidong Liu et al.
4 citations
Organic Letters
Sulfur-Based Synthesis Techniques
3.74
article

β-Thioamide Sulfone Enabled Copper-Catalyzed Ring-Opening/Sulfonylation of Cyclopropenes: Access to Alkyl Aryl Sulfones

Yi Kong, C.‐S. CHUNG, Qin Yin, Yidong Liu, Jingru Wang, Cheng‐Xiang Wang, Shaoquan Lin, Arshad Ali, Lang Liu
article en
4 citations

Abstract

Sulfone motifs play important roles in bioactive compounds and functional materials. The development of efficient methodologies for constructing sulfonyl-containing compounds has thus attracted considerable attention. Here, we introduce a protocol for the preparation of alkyl aryl sulfones under mild conditions. This protocol employs β-thioamide sulfone as a novel sulfone motif donor. It forms sulfinates in situ under basic conditions, which then undergo cross-coupling with the intermediates that were generated from ligand-free copper-catalyzed cyclopropenes (CPEs) ring opening.

Organic LettersVol. 27(3)
Chongqing University (CN), Shenzhen University (CN), Chinese Academy of Sciences (CN), Shenzhen Institutes of Advanced Technology (CN), Shenzhen Technology University (CN)
National Natural Science Foundation of China, Basic and Applied Basic Research Foundation of Guangdong Province
Clean water and sanitation
Openalex Percentile: Top 9%
Sulfur-Based Synthesis Techniques
3.74
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β-Thioamide Sulfone Enabled Copper-Catalyzed Ring-Opening/Sulfonylation of Cyclopropenes: Access to Alkyl Aryl Sulfones — Yi Kong, C.‐S. CHUNG, et al. · Organic Letters (2025) | TGRS Research Map | TGRS