Cobalt-catalyzed hydrothiolation of alkynes for the diverse synthesis of branched alkenyl sulfides

Alkenyl sulfides have gained increasing prominence in medicinal chemistry and materials. Hydrothiolation of alkynes for the diverse synthesis of alkenyl sulfides is an appealing method. Herein, we report a cobalt-catalyzed Markovnikov hydromethylthiolation of alkynes to afford branched alkenyl methylsulfanes with good yields and high regioselectivity. This method also enables the diverse synthesis of branched alkenyl sulfides. The reaction shows good functional group tolerance and could be scaled up. The mechanistic studies including control experiments, deuterium-labeling experiments, and Hammett plot indicated alkynes insertion followed by electrophilic thiolation pathway.

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Publication Details

Journal
Nature Communications
Published
2024-09-14
DOI
https://doi.org/10.1038/s41467-024-52249-x
Citations
12
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
3.00

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article

Cobalt-catalyzed hydrothiolation of alkynes for the diverse synthesis of branched alkenyl sulfides

Jiale Ying, Zhan Lu, Yan Tan
12 citations
Nature Communications
Sulfur-Based Synthesis Techniques
3.00
article

Cobalt-catalyzed hydrothiolation of alkynes for the diverse synthesis of branched alkenyl sulfides

Jiale Ying, Zhan Lu, Yan Tan
article en
12 citations

Abstract

Alkenyl sulfides have gained increasing prominence in medicinal chemistry and materials. Hydrothiolation of alkynes for the diverse synthesis of alkenyl sulfides is an appealing method. Herein, we report a cobalt-catalyzed Markovnikov hydromethylthiolation of alkynes to afford branched alkenyl methylsulfanes with good yields and high regioselectivity. This method also enables the diverse synthesis of branched alkenyl sulfides. The reaction shows good functional group tolerance and could be scaled up. The mechanistic studies including control experiments, deuterium-labeling experiments, and Hammett plot indicated alkynes insertion followed by electrophilic thiolation pathway.

Nature CommunicationsVol. 15(1)
Zhengzhou University (CN), Zhejiang University (CN)
National Natural Science Foundation of China, Fundamental Research Funds for the Central Universities, Natural Science Foundation of Zhejiang Province
Openalex Percentile: Top 8%
Sulfur-Based Synthesis Techniques
3.00
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Cobalt-catalyzed hydrothiolation of alkynes for the diverse synthesis of branched alkenyl sulfides — Jiale Ying, Zhan Lu, et al. · Nature Communications (2024) | TGRS Research Map | TGRS