Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (1): 189-198.DOI: 10.6023/cjoc202506011 Previous Articles     Next Articles

ARTICLES

半胱氨酸的硫杂芳基化反应

张鑫, 李飞, 周晨星, 霍聪德*()   

  1. 西北师范大学化学化工学院 兰州 730070
  • 收稿日期:2025-06-05 修回日期:2025-08-13 发布日期:2025-09-11
  • 通讯作者: 霍聪德
  • 基金资助:
    国家自然科学基金(22271234)

S-Heteroarylation of Cysteines

Zhang Xin, Li Fei, Zhou Chenxing, Huo Congde*()   

  1. College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070
  • Received:2025-06-05 Revised:2025-08-13 Published:2025-09-11
  • Contact: Huo Congde
  • Supported by:
    National Natural Science Foundation of China(22271234)

A new method for S-heteroarylation of cysteine derivatives using affordable, readily available chlorinated hetero- aromatic compounds has been proposed. The reaction proceeds via nucleophilic aromatic substitution (SNAr) under mild conditions and simple operation, exhibiting excellent tolerance to various functional groups and high chemical selectivity. The results of substrate scope investigation demonstrated that A wide range of substrates, including different N-protected cysteine derivatives, cysteine-containing peptides, and various chlorinated heteroaryl compounds, could be efficiently transformed via this protocol to afford the desired products in good yields. Scale-up experiments confirmed the practicality and eco-friendliness of this protocol. Overall, this strategy offers an efficient and selective approach to modify cysteine and other thiols under mild conditions with broad potential applications in protein modification and biomolecular labeling.

Key words: cysteine, heteroarylation, peptide