Citation: Haoyu Tian, Xiaolin Cui, Guiwei Yao, Wenyan Wei, Junchao Lu, Senyao Zheng, Xingjian Wang, Xun Chen, Guangkuan Zhao, Dulin Kong. The sulfenylation of enamine esters with heterocyclic thiols or disulfides in water and application to DNA-compatible chemistry[J]. Chinese Chemical Letters, ;2025, 36(12): 111006. doi: 10.1016/j.cclet.2025.111006 shu

The sulfenylation of enamine esters with heterocyclic thiols or disulfides in water and application to DNA-compatible chemistry

Engineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, International Joint Research Center of Human-machine Intelligent Collaborative for Tumor Precision Diagnosis and Treatment of Hainan Province, Hainan Provincial Key Laboratory of Research and Development on Tropical Herbs, School of Pharmaceutical Sciences, Hainan Medical University, Haikou 571199, China

chenxun@muhn.edu.cn

zhaoguangkuan@muhn.edu.cn

kongdulin@muhn.edu.cn

Received Date: 28 December 2024
Revised Date: 23 February 2025
Accepted Date: 26 February 2025
Available Online: 1 March 2025

Figures(6)

An efficient synthesis of α-thioenamine compounds via a K₂S₂O₈-promoted cross-dehydrogenative coupling reaction between heterocyclic thiols and enamine esters in an aqueous medium has been developed. The reaction showed good tolerance for enamine esters and heterocyclic thiols with various functional groups, producing α-thioenamine derivatives in moderate to high yields. Mechanistic studies revealed that heterocyclic thiols react with K₂S₂O₈ in water to form reactive disulfides in situ, which then react with enamine esters to generate a series of α-thioenamines. Building on the proposed mechanism, we developed a sulfenylation reaction of enamine esters with disulfides without the need for an oxidant. This oxidant-free approach has been successfully employed to synthesize DNA-tagged α-thioenamine, demonstrating its considerable potential for various synthetic applications.
- Aminothioalkene,
- Sulfenylation,
- Enamine ester,
- Thiol,
- Disulfide,
- Oxidant-free,
- Water
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