Acta Chimica Sinica ›› 2024, Vol. 82 ›› Issue (2): 171-189.DOI: 10.6023/A23100435 Previous Articles     Next Articles

Review

亚磺酸内酯研究进展

杨铃悦, 李赟婷, 舒超*()   

  1. 华中师范大学化学学院 绿色农药全国重点实验室 武汉 430079
  • 投稿日期:2023-10-01 发布日期:2023-11-24
  • 作者简介:

    杨铃悦, 就读于华中师范大学化学学院(导师: 舒超教授), 主要研究方向为自由基硫化学.

    李赟婷, 就读于华中师范大学化学学院(导师: 舒超教授), 主要研究方向为自由基硫化学.

    舒超, 华中师范大学化学学院、绿色农药全国重点实验室教授; 2017年博士毕业于厦门大学; 2017年至2021年在英国布里斯托大学从事博士后研究; 2021年至今在华中师范大学开展独立研究工作. 主要从事基于新型合成方法、合成设备、催化剂的有机功能分子精准合成和应用.

  • 基金资助:
    国家自然科学基金(22301093); 华中师范大学和武汉市科学技术局(20201037026)

Research Progress on Sultine

Lingyue Yang, Yunting Li, Chao Shu()   

  1. National Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, Wuhan 430079
  • Received:2023-10-01 Published:2023-11-24
  • Contact: E-mail: chaoshu@ccnu.edu.cn
  • Supported by:
    National Natural Science Foundation of China(22301093); Central China Normal University and Wuhan Science and Technology Bureau(20201037026)

Heterocycles are a highly valuable class of complex scaffolds that are involved in a various kind of well-known organic compounds of industrial and pharmacological importance. Sultine, an important class of sulfur-containing heterocyclic compounds, plays central roles in medicine, biology and material science. The sulfur atom in sultine is located at a vertex of a stable pyramid without identical substituents, making it a chiral center with potential applications in asymmetric synthesis. The asymmetry of sultine can be easily eliminated by oxidizing it into sultone. In addition, sultines have shown to be versatile intermediates in organic synthesis. They can act as useful synthons with hidden bifunctionality: opening the heterocycle at the S—O bond leads to the simultaneous appearance of two functional groups in the product. Despite their potential, the chemical research of sultines have been long neglected and underdeveloped due to their inaccessibility. Only recently, some research groups have discovered protocols for the preparation of these heterocycles and explored their properties using methods such as visible light-induced radical homolytic substitution cyclization and radical polar crossover cyclization, and so on. It is worth noting that although sultines have been discussed in a few reviews, they are not systematic but very fragmentary. Owing to the increasing interest in studies on sultines and their transformations. The synthesis methods, physical properties and applications of sultines are systematically summarized in the past 130 years. The synthetic tactics are reviewed by highlighting their product diversity, selectivity and applicability, along with the mechanistic rationale where possible. Additionally, the chemical transformations of sultines, including photolysis, thermolysis, ring-opening reactions, oxidation/reduction reactions, and rearrangement reactions, are demonstrated. The usefulness of sultines in synthesis, medicine and materials is described as well. Finally, the development status of sultine compounds is reviewed, and a future perspective is provided, in order to offer reference for researchers engaged in sultine chemistry.

Key words: sultine, synthesis, property, application