有机大共轭分子C-H亲核取代反应的研究进展

doi:10.6023/cjoc202509030

摘要/Abstract

有机大共轭分子凭借其独特的扩展π电子体系, 在材料化学、药物化学及化学生物学等领域展现出重要且广泛的应用价值. 对大共轭分子进行官能团化以调控其性质, 已成为化学研究领域备受关注的重要议题之一. 目前, 大共轭分子的后修饰方法研究相对较少, 主要依赖于芳香亲电取代和过渡金属催化的偶联反应等常规策略. 本文系统综述了基于大共轭分子的独特C-H亲核取代反应研究进展, 涵盖了经典体系如卟啉、BODIPYs、薁烯以及一些其他大共轭分子. 研究表明, 通过优化反应条件、选用合适的亲核试剂、导向基团与添加剂, 可以实现对特定C-H键的高效亲核取代官能团化, 从而构建具有特定结构与功能的化合物. 本文不仅将深化对亲核取代反应机制的理解, 还为构建具有独特功能的π共轭体系开辟了新途径.

关键词: 大共轭分子, π-电子体系, 亲核取代, C-H官能团化

Organic largely conjugated molecules, characterized by their delocalized π-electron systems, exhibit significant and broad application potential in fields such as materials chemistry, medicinal chemistry, and chemical biology. Functionalizing these conjugated systems to modulate their properties has become a major focus in chemical research. However, current methods for late-stage modification of extended conjugated molecules remain limited, primarily relying on conventional strategies such as electrophilic aromatic substitution and transition-metal-catalyzed coupling reactions. This review systematically summarizes recent advances in unique C-H nucleophilic substitution reactions on extended conjugated molecules, covering classical systems such as porphyrins, BODIPYs, azulene, and some other large conjugated molecules. Studies have demonstrated that by optimizing reaction conditions, selecting suitable nucleophiles, and employing directing groups, efficient functionalization of specific C-H bonds can be achieved, enabling the construction of compounds with tailored structures and functions. This review not only deepens the understanding of nucleophilic substitution mechanisms but also opens new avenues for designing π-conjugated systems with unique functionalities.

Key words: largely conjugated systems, π-electron system, nucleophilic substitutions, C-H functionalization

引用此文

白燕茹, 周来运, 刘广华, 王青. 有机大共轭分子C-H亲核取代反应的研究进展[J]. 有机化学, doi: 10.6023/cjoc202509030.

Bai Yanru, Zhou Laiyun, Liu Guanghua, Wang Qing. Research Progress on C-H Nucleophilic Substitution Reactions of Organic Largely Conjugated Molecules[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202509030.

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