有机化学 ›› 2023, Vol. 43 ›› Issue (11): 3761-3783.DOI: 10.6023/cjoc202303042 上一篇    下一篇

综述与进展

芳香卤代物C—S偶联反应的研究进展

秦思凝*()   

  1. 沈阳大学师范学院化学系 沈阳 110044
  • 收稿日期:2023-03-29 修回日期:2023-05-31 发布日期:2023-06-26

Research Progress in C—S Coupling Reactions of Aryl Halides

Sining Qin()   

  1. Department of Chemistry, Normal College, Shenyang University, Shenyang 110044
  • Received:2023-03-29 Revised:2023-05-31 Published:2023-06-26
  • Contact: E-mail: qinsining2003@163.com

含硫化合物在天然产物、药物、农药和材料中广泛存在, 具有多种生物活性或独特功能. C—S偶联反应是合成含硫化合物的重要方法, 是有机合成领域的研究热点之一. 随着对催化剂的深入开发和对含硫偶联反应物的不断扩展, 近年来涌现出大量的C—S偶联反应方法, 为含硫化合物的合成提供了便利. 芳香卤代烃是合成含硫化合物的主要底物, 通过设计不同的反应体系和含硫偶联反应物进行C—S偶联反应, 能够高效地合成硫酚、硫醚、二硫醚和砜等含硫化合物. 按照不同种类的含硫偶联反应物类型和催化剂种类(钯、铜和镍等)进行分类, 综述了近年来以芳香卤代烃为底物的C—S偶联反应, 并对代表性反应的机理做了简要说明和比较. 此外, 还对这一领域目前存在的问题和局限性进行简要分析, 并对未来发展方向提出展望.

关键词: C—S偶联反应, 芳香卤代物, 含硫化合物, 过渡金属催化剂

Sulfur-containing compounds are widely found in natural products, pharmaceuticals, pesticides, and materials, possessing a variety of biological activities or unique functions. C—S coupling reaction is an important method for the synthesis of sulfur-containing compounds and is one of the hot spots in the field of organic synthesis. With the in-depth development of catalysts and the continuous expansion of sulfur-containing coupling partners, a large number of C—S coupling reactions have emerged in recent years, which greatly facilitate the synthesis of sulfur-containing compounds. Aryl halides are the main kind of substrates for the synthesis of sulfur-containing compounds. C—S coupling reactions of aryl halides and sulfur-containing coupling partners can efficiently afford sulfur-containing compounds, such as thiophenols, thioethers, disulfides and sulfones in different well-designed reaction systems. In this review, the C—S coupling reactions with aryl halides as substrates are reviewed according to the different types of sulfur-containing coupling partners and catalysts (palladium, copper, nickel, and others). The mechanisms of representative reactions are briefly described and compared. In addition, a brief analysis of the current situations and limitations in this field is given, and a prospect for future development is put forward.

Key words: C—S coupling reaction, aryl halide, sulfur-containing compounds, transition-metal catalyst