Citation: Hao Xu, Xufeng Li, Jie Ma, Junze Zuo, Xiuyan Song, Jian Lv, Daoshan Yang. An electron donor–acceptor photoactivation strategy for the synthesis of S-aryl dithiocarbamates using thianthrenium salts under mild aqueous micellar conditions[J]. Chinese Chemical Letters, ;2023, 34(11): 108403. doi: 10.1016/j.cclet.2023.108403 shu

An electron donor–acceptor photoactivation strategy for the synthesis of S-aryl dithiocarbamates using thianthrenium salts under mild aqueous micellar conditions

Hao Xu ^a ,
Xufeng Li ^b ,
Jie Ma ^a ,
Junze Zuo ^a ,
Xiuyan Song ^a ,
Jian Lv ^a ,
Daoshan Yang ^{a, c, *,}

a.
Key Laboratory of Optic-electric Sensing and Analytical Chemistry for Life Science, MOE, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
b.
Zhejiang Wansheng Co., Ltd., Linhai 317000, China
c.
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China

^☆

yangdaoshan@tsinghua.org.cn

Received Date: 29 December 2022
Revised Date: 18 March 2023
Accepted Date: 28 March 2023
Available Online: 30 March 2023

Figures(7)

An eco-friendly and convenient method is developed herein for the synthesis of S-aryl dithiocarbamates via visible-light-induced SET process of an EDA complex between thianthrenium salt functionalized arenes and dithiocarbamate anions under mild aqueous micellar conditions. This strategy indirectly realizes the method for constructing S-aryl dithiocarbamates through site-selective C−H functionalization of arenes. Most importantly, the reaction proceeded smoothly without addition of any photocatalyst, and the by-product thianthrene is recycled in quantity, ultimately minimizing the production of chemical waste. This protocol provides a promising synthesis candidate for the construction of valuable S-aryl dithiocarbamates, which also opens up a new avenue for micellar photocatalysis.
- S-Aryl dithiocarbamates,
- Visible-light,
- EDA complex,
- Thianthrenium salts,
- Micellar photocatalysis
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