Conversion of Acids to <i>S</i>-Alkyl Dithiocarbamates by Decarboxylative Sulfuration Using Visible-Light Photocatalysis

<i>S</i>-Alkyl dithiocarbamates, as an important class of sulfur-containing compounds, play pivotal roles in diverse fields, yet methods for the synthesis that start from simple, readily available feedstocks and exhibit mild conditions and structurally diverse products are scarce. In this work, we developed an efficient approach for the synthesis of various <i>S</i>-alkyl dithiocarbamates via visible-light photocatalysis with readily available and structurally diverse alkyl carboxylic acids (primary, secondary, and tertiary acids, amino acids, etc.) and disulfide tetraalkylthiuram as the starting materials. This protocol features high efficiency, mild reaction conditions, a broad substrate scope, and good functional group tolerance. Potential applications are further demonstrated by a sunlight experiment, H<sub>2</sub>O as a solvent, gram-scale synthesis, and facile synthesis of bioactive molecules.

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Publication Details

Journal
Organic Letters
Published
2024-09-23
DOI
https://doi.org/10.1021/acs.orglett.4c03028
Citations
8
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
2.00

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article

Conversion of Acids to S-Alkyl Dithiocarbamates by Decarboxylative Sulfuration Using Visible-Light Photocatalysis

Yu−Xi Wu, Xing‐Xing Yang, Zhi‐Bing Dong, Zhipeng Guan et al.
8 citations
Organic Letters
Sulfur-Based Synthesis Techniques
2.00
article

Conversion of Acids to S-Alkyl Dithiocarbamates by Decarboxylative Sulfuration Using Visible-Light Photocatalysis

Yu−Xi Wu, Xing‐Xing Yang, Zhi‐Bing Dong, Zhipeng Guan, Yaoyao Li, Shiyi Zhao, Zhong-Qi Yi
article en
8 citations

Abstract

<i>S</i>-Alkyl dithiocarbamates, as an important class of sulfur-containing compounds, play pivotal roles in diverse fields, yet methods for the synthesis that start from simple, readily available feedstocks and exhibit mild conditions and structurally diverse products are scarce. In this work, we developed an efficient approach for the synthesis of various <i>S</i>-alkyl dithiocarbamates via visible-light photocatalysis with readily available and structurally diverse alkyl carboxylic acids (primary, secondary, and tertiary acids, amino acids, etc.) and disulfide tetraalkylthiuram as the starting materials. This protocol features high efficiency, mild reaction conditions, a broad substrate scope, and good functional group tolerance. Potential applications are further demonstrated by a sunlight experiment, H<sub>2</sub>O as a solvent, gram-scale synthesis, and facile synthesis of bioactive molecules.

Organic LettersVol. 26(39)
Henan Normal University (CN), Wuhan Institute of Technology (CN)
National Natural Science Foundation of China, Natural Science Foundation of Hubei Province
Clean water and sanitation
Openalex Percentile: Top 14%
Sulfur-Based Synthesis Techniques
2.00
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Conversion of Acids to <i>S</i>-Alkyl Dithiocarbamates by Decarboxylative Sulfuration Using Visible-Light Photocatalysis — Yu−Xi Wu, Xing‐Xing Yang, et al. · Organic Letters (2024) | TGRS Research Map | TGRS