Copper-Catalyzed Sulfinylation of Boronic Acids with Sulfinates

A copper-catalyzed sulfinylation of boronic acids with sulfinates was achieved to access a range of aryl/alkenyl sulfoxides. Dialkyl dicarbonates served as the key activator, effectively promoting the desired sulfinylation process and suppressing the undesired pathway to the thiosulfonate byproduct. Preliminary mechanistic studies indicated that this transformation favors a copper-mediated nucleophilic substitution over a Suzuki-type cross-coupling process. This protocol paves the way for the metal-catalyzed establishment of a C-S(=O) bond from readily available sulfinates.

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Publication Details

Journal
Organic Letters
Published
2025-11-21
DOI
https://doi.org/10.1021/acs.orglett.5c04675
Citations
1
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.94
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article

Copper-Catalyzed Sulfinylation of Boronic Acids with Sulfinates

Jie Wu, Ming‐Hua Xu, Xinhua Wang, Jun Zhang et al.
1 citations
Organic Letters
Sulfur-Based Synthesis Techniques
0.94
article

Copper-Catalyzed Sulfinylation of Boronic Acids with Sulfinates

Jie Wu, Ming‐Hua Xu, Xinhua Wang, Jun Zhang, Xiaoyu Zhou, Hui-Ling Ma, S.G. Ma
article en
1 citations

Abstract

A copper-catalyzed sulfinylation of boronic acids with sulfinates was achieved to access a range of aryl/alkenyl sulfoxides. Dialkyl dicarbonates served as the key activator, effectively promoting the desired sulfinylation process and suppressing the undesired pathway to the thiosulfonate byproduct. Preliminary mechanistic studies indicated that this transformation favors a copper-mediated nucleophilic substitution over a Suzuki-type cross-coupling process. This protocol paves the way for the metal-catalyzed establishment of a C-S(=O) bond from readily available sulfinates.

Organic LettersVol. 27(48)
Chinese Academy of Sciences (CN), Shanghai Institute of Organic Chemistry (CN), Henan Normal University (CN), Taizhou University (CN)
Openalex Percentile: Top 19%
Sulfur-Based Synthesis Techniques
0.94
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Copper-Catalyzed Sulfinylation of Boronic Acids with Sulfinates — Jie Wu, Ming‐Hua Xu, et al. · Organic Letters (2025) | TGRS Research Map | TGRS