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Synlett
DOI: 10.1055/s-0043-1775431
DOI: 10.1055/s-0043-1775431
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The Versatility of Nickel: Advances in C–S Bond Formation
We are grateful to the National Natural Science Foundation of China (21971174), PAPD, Cyrus Tang (Zhongying) Scholar, the Jiangsu Qing-Lan Project for Young and Middle-Aged Academic Leaders (2023) andSoochow University for financial support.
Abstract
Nickel-catalyzed carbon–sulfur (C–S) bond formation is a key process in organic synthesis, being widely applied in pharmaceuticals, agrochemicals, and materials science. This account summarizes recent advances in Ni-catalyzed C–S bond construction, covering key factors such as ligand choice, solvent, and temperature, which affect yield and selectivity. Case studies illustrate the scope of the methods in producing complex molecules. Remaining challenges include broadening the substrate scope and enhancing the selectivity for the formation of asymmetric C–S bonds. This account concludes with future directions, emphasizing the need for more efficient catalysts to expand the role of nickel in synthetic chemistry.
1 Introduction
2 Synthetic Method Development
2.1 A Novel Methodology for Thiolation and Selenylation Reactions
2.2 Nickel-Catalyzed Reductive Coupling and SN2 Reaction for Sulfides/Selenides and Sulfones
2.3 Efficient Nickel-Catalyzed Reductive Coupling for Unsymmetrical Disulfides
2.4 A Convenient Approach to Thioesters and Acyl Disulfides via Nickel-Catalyzed Reduction
2.5 Ligand-Controlled Nickel-Catalyzed Access to Disulfides from Dithiosulfonates and Alkyl Halides
3 Conclusion and Outlook
Key words
cross-coupling reaction - nickel-mediated transformations - thiolation - sustainable bond-forming strategies - C–S linkagePublication History
Received: 11 November 2024
Accepted after revision: 09 December 2024
Article published online:
02 September 2025
© 2025. Thieme. All rights reserved
Georg Thieme Verlag KG
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