Photoinduced Decarboxylative Thioacylation of <i>N</i>‐Hydroxyphthalimide Esters with Tetraalkylthiuram Disulfides

Dithiocarbamate is a key structural sequence in pharmaceuticals and agrochemicals, and its synthesis is crucial in organic chemistry. Although significant progress has been made in related synthesis research, developing a practical and universal synthesis method remains fascinating. Herein, we report a new visible-light-induced decarboxylation coupling reaction between N-hydroxyphthalimide esters and tetraalkylthiuram disulfides, which uses Ir(ppy)<sub>3</sub> as a photocatalyst to promote the generation of corresponding decarboxylation thioacylation product-dithiocarbamates in high yields. This redox-neutral protocol uses inexpensive and readily available starting material under mild reaction conditions, exhibiting broad substrate scope and wide functional group compatibility. This method can be further used for post modification of complex natural products and bioactive drugs.

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Publication Details

Journal
Chemistry - A European Journal
Published
2024-08-21
DOI
https://doi.org/10.1002/chem.202402716
Citations
2
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.50

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article

Photoinduced Decarboxylative Thioacylation of N‐Hydroxyphthalimide Esters with Tetraalkylthiuram Disulfides

Ying‐Ming Pan, Yujing Zhou, Jing‐Chen Jiang, Haitao Tang et al.
2 citations
Chemistry - A European Journal
Sulfur-Based Synthesis Techniques
0.50
article

Photoinduced Decarboxylative Thioacylation of N‐Hydroxyphthalimide Esters with Tetraalkylthiuram Disulfides

Ying‐Ming Pan, Yujing Zhou, Jing‐Chen Jiang, Haitao Tang, Fei‐Hu Cui, Wengui Duan, C. C. Zhang, Yanfei Li, Qian Wang
article en
2 citations

Abstract

Dithiocarbamate is a key structural sequence in pharmaceuticals and agrochemicals, and its synthesis is crucial in organic chemistry. Although significant progress has been made in related synthesis research, developing a practical and universal synthesis method remains fascinating. Herein, we report a new visible-light-induced decarboxylation coupling reaction between N-hydroxyphthalimide esters and tetraalkylthiuram disulfides, which uses Ir(ppy)<sub>3</sub> as a photocatalyst to promote the generation of corresponding decarboxylation thioacylation product-dithiocarbamates in high yields. This redox-neutral protocol uses inexpensive and readily available starting material under mild reaction conditions, exhibiting broad substrate scope and wide functional group compatibility. This method can be further used for post modification of complex natural products and bioactive drugs.

Chemistry - A European JournalVol. 30(68)
Guangxi University (CN), Guangxi Normal University (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 40%
Sulfur-Based Synthesis Techniques
0.50
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Photoinduced Decarboxylative Thioacylation of <i>N</i>‐Hydroxyphthalimide Esters with Tetraalkylthiuram Disulfides — Ying‐Ming Pan, Yujing Zhou, et al. · Chemistry - A European Journal (2024) | TGRS Research Map | TGRS