Citation: Guoju Guo, Xufeng Li, Jie Ma, Yongjia Shi, Jian Lv, Daoshan Yang. Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation[J]. Chinese Chemical Letters, ;2024, 35(11): 110024. doi: 10.1016/j.cclet.2024.110024 shu

Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation

Guoju Guo ^a ,
Xufeng Li ^b ,
Jie Ma ^a ,
Yongjia Shi ^a ,
Jian Lv ^a ,
Daoshan Yang ^{a, c, *,}

a.
College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
b.
Zhejiang Wansheng Co. Ltd., Linhai 317000, China
c.
National Engineering Research Center of Low-Carbon Processing and Utilization of Forest Biomass, Nanjing Forestry University, Nanjing 210037, China

yangdaoshan@tsinghua.org.cn

Received Date: 11 March 2024
Revised Date: 9 May 2024
Accepted Date: 16 May 2024
Available Online: 17 May 2024

Figures(6)

A photocatalyst-free visible-light-promoted three-component reaction of thianthrenium salts, isothiocyanates, and amines is presented, which affords a rapid and efficient approach to S-arylisothioureas under mild conditions. This developed method exhibits the advantages of readily available raw materials, broad substrate scope, good functional tolerance, and operational simplicity. It is worth mentioning that the byproduct thianthrene can be recycled in quantity, ultimately maximizing the atomic economy of the reaction and avoiding chemical waste. Mechanism investigations support the strategy involving a photoinduced EDA complex.
- Visible-light,
- Photocatalyst-free,
- EDA complex,
- Thianthrenium salts,
- S-arylisothioureas
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