Intramolecular dearomative [2π + 2σ] photocycloadditions of bicyclo[1.1.0]butanes with (benzo)furans and (benzo)thiophenes initiated by energy transfer or single electron transfer

IF 9.7 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Science China Chemistry Pub Date : 2025-06-23 DOI:10.1007/s11426-025-2704-x

Yuyue Li, Xintao Gu, Yin Wei, Min Shi

引用次数: 0

Abstract

Dearomative photocycloaddition of heteroarenes is an efficient method for replacing planar arenes with three-dimensional (3D) scaffolds, such as bicyclo[2.1.1]-hexane (BCH) containing heterocycles. Herein, we report intramolecular dearomative [2π + 2σ] photocycloadditions of bicyclo[1.1.0]butanes (BCBs) with (benzo)furans and (benzo)thiophenes. These photocycloadditions are initiated through an energy transfer pathway (EnT) or single electron transfer pathway (SET), efficiently yielding unique BCH-pyrrolidinone-fused heterocyclic scaffolds. Moreover, the synthetic utility of this photochemical reaction was demonstrated on the basis of large-scale synthesis and diversified transformations. Mechanistic investigations, in conjunction with density functional theory (DFT) calculations, were taken to support the proposed reaction mechanisms.

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以能量转移或单电子转移引发双环[1.1.0]丁烷与（苯并）呋喃和（苯并）噻吩的分子内脱芳[2π + 2σ]光环加成反应

杂环芳烃的脱芳光环加成是用三维（3D）支架取代平面芳烃的有效方法，如含杂环的双环[2.1.1]-己烷（BCH）。本文报道了双环[1.1.0]丁烷（BCBs）与（苯并）呋喃和（苯并）噻吩的分子内脱芳[2π + 2σ]光环加成反应。这些光环添加通过能量转移途径（EnT）或单电子转移途径（SET）启动，有效地产生独特的bch -吡咯烷酮融合杂环支架。此外，在大规模合成和多样化转化的基础上，证明了该光化学反应的合成用途。力学研究，结合密度泛函理论（DFT）计算，采取支持提出的反应机制。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Science China Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

14.40

自引率

7.30%

发文量

3787

审稿时长

2.2 months

期刊介绍： Science China Chemistry, co-sponsored by the Chinese Academy of Sciences and the National Natural Science Foundation of China and published by Science China Press, publishes high-quality original research in both basic and applied chemistry. Indexed by Science Citation Index, it is a premier academic journal in the field. Categories of articles include: Highlights. Brief summaries and scholarly comments on recent research achievements in any field of chemistry. Perspectives. Concise reports on thelatest chemistry trends of interest to scientists worldwide, including discussions of research breakthroughs and interpretations of important science and funding policies. Reviews. In-depth summaries of representative results and achievements of the past 5–10 years in selected topics based on or closely related to the research expertise of the authors, providing a thorough assessment of the significance, current status, and future research directions of the field.