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<p>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.</p>

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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

  • 期刊论文

  • 发表日期：

    2025年6月23日

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  • Yuyue Li,
  • Xintao Gu,
  • Yin Wei,
  • Min Shi

摘要

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.