本文旨在开发一种利用廉价、易得的氯代杂芳烃,对半胱氨酸衍生物进行S-杂芳基化的新方法. 该方法基于亲核芳香取代(SNAr)反应,操作简便,条件温和,具有优异的官能团兼容性和高化学选择性. 底物范围广泛,包括多种N-保护基的半胱氨酸衍生物、含半胱氨酸的寡肽及多样的氯代杂芳基化合物,均获得良好产率. 放大实验进一步验证了该方法的实用性和绿色环保性. 该策略为温和条件下高效、选择性修饰半胱氨酸及其他硫醇分子提供了新途径,展现出在蛋白质修饰和生物分子标记等领域的广阔应用前景.
This study presents a new method for S-heteroarylation of cysteine derivatives using affordable, readily available chlorinated heteroaromatic compounds. 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. A wide range of substrates was tested, including different N-protected cysteine derivatives, cysteine-containing peptides, and various chlorinated heteroaryl compounds, all yielding good results. Scale-up experiments confirmed the method’s practicality and its environmentally friendly nature. 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.
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