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DOI: https://doi.org/10.6023/A26030079

综述

双环[1.1.0]丁烷衍生物在去芳构化环加成构建立体多环分子中的应用

  • 韩宇 ,
  • 宋钦华
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  • 化学与材料科学学院 中国科学技术大学 安徽合肥 230026
韩宇,男,中国科学技术大学2025级研究生,研究兴趣为有机合成方法学,主要研究内容涉及光诱导的自由基反应用于芳烃去芳构化与功能分子的合成; 宋钦华,中国科学技术大学教授、博士生导师,长期致力于有机分子探针的设计、合成与应用以及有机光催化自由基反应的研究

收稿日期: 2026-03-19

  网络出版日期: 2026-06-25

基金资助

项目得到国家自然科学基金项目(22074135)支持

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Applications of Bicyclo[1.1.0]butanes Mediated Dearomative Cycloadditions for the Construction of 3D polycyclic Molecules

  • Han Yu ,
  • Song Qinhua
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  • School of Chemistry and Materials Science, University of Science and Technology of China, Hefei, Anhui 230026

Received date: 2026-03-19

  Online published: 2026-06-25

Supported by

National Natural Science Foundation of China (22074135).

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摘要

具有季碳中心的三维饱和多环单元的有机化合物在医药、生物、化工、材料、不对称有机合成、农学等领域均有着重要的价值与应用潜力。然而,低效且冗长的传统合成策略一直制约着此类化合物的深入研究与实际应用。二维(杂)芳香烃化合物作为此类化合物的潜在反应前体因其固有的反应惰性致使研究其直接进行“升维”转变原位构建富含Csp3的三维有机化合物成为了一种极具挑战性的工作。在二十一世纪以来的绿色有机合成、催化、医药、生物等领域的交叉研究中,具有特殊结构的双环[1.1.0]丁烷衍生物(BCBs)作为一种颇具潜力的多功能分子砌块,在高效转变(杂)芳香烃化合物为具有更高实用价值的三维多环复杂分子方面被逐步证实并由此发展出了一系列新的合成策略。在此,系统性地总结与概述了近年来借助Lewis酸催化、有机光催化及其他催化体系下的利用BCBs实现对(杂)芳烃[σ+π]环加成去芳构化构建立体多环分子的研究进展并对其后续富有前景的研究与发展进行了展望。

关键词： 双环[1.1.0]丁烷衍生物; [σ+π]环加成; Lewis酸催化; 有机光催化; (杂)芳烃去芳构化; 三维多环分子

本文引用格式

韩宇 , 宋钦华 . 双环[1.1.0]丁烷衍生物在去芳构化环加成构建立体多环分子中的应用[J]. 化学学报, 0 : 30079 -30079 . DOI: 10.6023/A26030079

Abstract

Organic compounds containing three-dimensional saturated polycyclic units with quaternary carbon centres hold significant value and application potential in fields such as medicine, biology, chemical engineering, materials science, asymmetric organic synthesis and agriculture. In recent years, the successful application in clinical trials of innovative drug molecules and bioactive molecules designed and developed using the ‘escape from flatland' concept in medicinal chemistry, as well as analogues of bioisosteric scaffolds containing aromatic rings synthesised using bioisosterism, has brought these molecules to the forefront of attention in numerous fields of research. However, the limited availability of direct natural sources and inefficient and time-consuming traditional synthetic strategies have consistently hindered the research and practical application of such compounds. Although two-dimensional (hetero)aromatics—which are diverse, widely sourced, and largely inexpensive and readily available—serve as potential reaction precursors for these compounds, their inherent reactivity inertness makes it an extremely challenging task to study their direct ‘dimensional upgrade' transformation to in situ construct Csp3-rich three-dimensional organic scaffolds. In interdisciplinary research across fields such as green organic synthesis, catalysis, pharmaceuticals and biology since the beginning of the 21st century, bicyclo[1.1.0]butane derivatives (BCBs)—with their unique structures—have emerged as highly potential, multifunctional molecular building blocks. Their efficacy in efficiently transforming (hetero)aromatic compounds into three-dimensional polycyclic complex molecules of greater practical value has been progressively demonstrated, leading to the development of a series of novel synthetic strategies. Herein, we systematically summarize and overview progress made over the past years in the utilization of bicyclo[1.1.0]butane derivatives for (hetero)aromatics dearomatisation and construction of 3D cyclic polycyclic molecules via cycloaddition reaction under Lewis acid catalysis, visible-light-driven organic catalysis (including energy-transfer catalysis and single electron transfer catalysis) and other hybrid catalytic systems, covering more than twenty cases, and also provide an outlook on promising future research and developments in this field facilitating a wider application of three-dimensional polycyclic molecules and emergence of novel design ideas.

Key words： bicyclo[1.1.0]butanes; [σ+π] cycloaddition; Lewis acid catalysis; organic photocatalysis; (hetero)aromatic dearomatisation; 3D polycyclic molecule

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