自由基介导的官能团迁移-环化构建含氮稠杂芳烃

doi:10.6023/cjoc202512005

摘要/Abstract

含氮杂环是药物及许多功能分子的核心骨架,其高效合成始终是有机化学的关键问题。自由基介导的官能团迁移（FGM）策略为烯烃的双官能团化提供了强大工具。本文中,我们利用官能团迁移-环化串联策略,发展一种步骤经济且条件温和的含氮稠杂环合成新方法。基于我们前期对对接-迁移反应研究的积累,通过对关键连接单元的理性设计,成功开发了一类新型的基于亚砜的杂环化试剂。在温和的可见光照射条件下,该试剂能与多种烯烃发生高效的自由基对接-迁移反应,并引发分子内的串联环化过程,一步实现多种含氮稠杂芳烃的模块化构建。反应可在温和的条件下进行,底物普适性广、官能团兼容性优异,为复杂药物活性分子的后期修饰提供了绿色、高效的合成工具。

关键词: 自由基反应, 含氮稠杂芳烃, 官能团迁移, 光反应, 环化反应

Nitrogen-containing heteroarenes constitute privileged scaffolds in pharmaceuticals and functional molecules, and their efficient synthesis remains a longstanding objective in organic chemistry. Over the past decade, radical-mediated functional group migration (FGM) has emerged as a powerful strategy for alkene functionalization. Herein, we report a step-economical and practical method for synthesizing N-heteroarenes directly from alkenes through a functional group migration-cyclization cascade. A new class of heterocyclizing agents featuring a sulfoxide linkage has been designed for this transformation. Under visible-light irradiation, these reagents engage with various alkenes in a radical “dock-migration” process, followed by intramolecular cyclization, enabling the modular construction of diverse N‑fused heteroarenes in a single operation. The reaction proceeds under mild conditions, exhibits broad substrate scope and excellent functional group tolerance, and offers a green, efficient synthetic tool for the late-stage modification of complex bioactive molecules.

Key words: radical reactions, N-fused heteroarenes, functional group migration, photocatalysis, cyclization reactions

引用此文

杨珊, 陈亚苏, 朱晨. 自由基介导的官能团迁移-环化构建含氮稠杂芳烃[J]. 有机化学, doi: 10.6023/cjoc202512005.

Yang Shan,chen Yasu, Zhu Chen. Access to N-Fused Heteroarenes via Radical-Mediated Functional Group Migration-Cyclization Cascade[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202512005.

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