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Updated: Jun 4, 2025

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Published on: April 9, 2018
Collaborative Reduction-Induced Nickel-Catalytic Selective C-S Coupling of Aryl Di/Trithiosulfonates with Aryl
Lulu Liu1, Jiaqi Hou1, Yingying Ma1
1Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710127, People's Republic of China.
This study introduces a novel nickel-catalyzed reaction for selective C-S coupling using aryl di/trithiosulfonates and aryl halides. The method efficiently produces sulfides, overcoming challenges in polysulfide reagent activation.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Metal-catalyzed conversion of polysulfide reagents presents challenges in activating multiple S-S bonds.
- The use of aryl di- and trithiosulfonates in nickel-catalyzed reductive coupling with aryl halides remains unexplored.
Purpose of the Study:
- To develop an unprecedented nickel-catalyzed method for selective C-S coupling.
- To utilize aryl di/trithiosulfonates with aryl halides for sulfide synthesis.
Main Methods:
- Nickel-catalyzed reductive coupling reaction.
- Utilized triphenylphosphine (PPh3) and zinc (Zn) for collaborative reduction.
- Employed magnesium chloride (MgCl2) to enhance reduction potential.
Main Results:
- Achieved selective C-S coupling of aryl di/trithiosulfonates with aryl halides.
- Successfully synthesized sulfides, avoiding disulfide or trisulfide formation.
- Demonstrated controllable reductive cleavage of PhSO2(S)n-aryl (n=2, 3) to electrophilic sulfur species.
Conclusions:
- The developed method offers a new pathway for sulfide synthesis.
- The PPh3 and Zn collaborative reduction, enhanced by MgCl2, is key to selective C-S bond formation.
- This work expands the scope of nickel-catalyzed cross-coupling reactions.
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