Synthesis of Thioureas from Amines and CS2 via Photoredox Catalysis

doi:10.6023/cjoc202405007

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (1): 240-245.DOI: 10.6023/cjoc202405007 Previous Articles Next Articles

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光催化胺与二硫化碳合成硫脲

李伟, 王奕森, 周荣, 高文超^*()

太原理工大学化学与化工学院太原 030024

收稿日期:2024-05-07 修回日期:2024-07-02 发布日期:2024-08-30
基金资助:
国家自然科学基金(21901179)

Synthesis of Thioureas from Amines and CS₂ via Photoredox Catalysis

Wei Li, Yisen Wang, Rong Zhou, Wenchao Gao()

College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024

Received:2024-05-07 Revised:2024-07-02 Published:2024-08-30
Contact: *E-mail: gaowenchao@tyut.edu.cn
Supported by:
National Natural Science Foundation of China(21901179)

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Abstract

In recent years, photocatalysis has become an important tool to construct new compounds in synthetic and pharmaceutical chemistry. In this work, various symmetric and unsymmetric thioureas were successfully synthesized by photoredox catalysis using CS₂ as thiocarbonyl source. For the mechanism, thiyl radicals were generated via single electron transfer process under photoredox catalysis after the nucleophilic addition of amines to CS₂, and then dimerized to reactive disulfides, which reacted with the other amines to form thioureas. The method features mild conditions, good functional group tolerance, and simple operation.

Key words: photochemistry, thioureas, carbon disulfide, green synthesis

Cite this article

Wei Li, Yisen Wang, Rong Zhou, Wenchao Gao. Synthesis of Thioureas from Amines and CS₂ via Photoredox Catalysis[J]. Chinese Journal of Organic Chemistry, 2025, 45(1): 240-245.

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Fig. & Tab. 5

Figure 1. Drugs and natural products containing thiourea structures and the activity comparation

Figure 2. Synthetic methods for thiourea compounds

Entry	Solvent	Base	Yield^b/%
1	H₂O	—	Trace
2	EtOAc	—	25
3	CH₃CN	—	43
4	CH₃CN	DABCO	78
5^c	CH₃CN	DABCO	95

Table 1. Reaction condition optimization for the synthesis of 3a

Table 2. Substrate scope for the synthesis of thioureas

Figure 3. Control experiments and proposed mechanism (a) Intermediate capture reaction; (b) Stern-Volmer quenching study; (c) Proposed catalytic cycle

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光催化胺与二硫化碳合成硫脲

Synthesis of Thioureas from Amines and CS₂ via Photoredox Catalysis

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