大学化学 >> 2025, Vol. 40 >> Issue (4): 239-244.doi: 10.12461/PKU.DXHX202406090

所属专题: “双碳”战略与化学

知识介绍 上一篇    下一篇

铜催化Kharasch-Sosnovsky型反应构筑碳氧键

王芃梓, 肖文精, 陈加荣   

  1. 华中师范大学化学学院, 武汉 430079
  • 收稿日期:2024-06-24 录用日期:2024-07-22 发布日期:2025-04-25
  • 通讯作者: 陈加荣J E-mail:chenjiarong@mail.ccnu.edu.cn
  • 基金资助:
    国家自然科学基金面上项目(22171099)

Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction

Pengzi Wang, Wenjing Xiao, Jiarong Chen   

  1. College of Chemistry, Central China Normal University, Wuhan 430079, China
  • Received:2024-06-24 Accepted:2024-07-22 Published:2025-04-25
  • Contact: Jiarong Chen E-mail:chenjiarong@mail.ccnu.edu.cn

摘要: 过渡金属催化的碳-杂原子偶联反应是有机合成化学中一个重要的研究方向。Kharasch-Sosnovsky反应利用过氧苯甲酸叔丁酯作为氧化剂,在金属铜催化的条件下,将烯烃转化为烯丙酯类化合物,完成碳氧键构筑。响应国家“双碳”战略,开发新的催化体系,实现含碳物质的绿色高效转化已经成为有机化学家们追求的重要目标。基于此,Kharasch-Sosnovsky反应在不对称反应、配体设计、底物范围扩展以及环境友好性方面取得了显著的改进。本文简要介绍了Kharasch-Sosnovsky反应的发现与新的研究进展,结合前沿科研成果,不仅有助于加深学生对基础有机化学中相关内容的理解,同时可以有效补充现有教材中的知识空缺,实现基础化学知识与学科前沿研究的深度融合。

关键词: Kharasch-Sosnovsky反应, 铜催化, 烯烃氧化, 不对称自由基反应

Abstract: Transition metal-catalyzed carbon-heteroatom bond formation is a crucial area in synthetic organic chemistry. The Kharasch-Sosnovsky reaction, catalyzed by copper, facilitates the conversion of olefins to allylic esters using tert-butyl peroxybenzoate as both an oxidant and oxygen source. In line with the “National Dual-Carbon Strategy”, the development of green and efficient catalytic systems for carbon-based transformations has become a key focus in organic chemistry. In this context, the Kharasch-Sosnovsky-type reaction has witnesses notable advances regarding asymmetric versions, ligand design, substrate scope expansion, and sustainable conditions. By surveying the cutting-edge chemical research, this paper presents a concise overview of the discovery and new progress of Kharasch-Sosnovsky reaction. It is hoped that this review can not only enhance students’ comprehension of fundamental organic chemistry concepts, but also effectively fill the gaps in existing textbooks, achieving a deep integration of basic chemical knowledge with cutting-edge research in the discipline.

Key words: Kharasch-Sosnovsky reaction, Copper catalysis, Olefin oxidation, Asymmetric radical reaction