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DOI: https://doi.org/10.6023/A26070250

Article

Visible-Light-Induced SO2 Insertion/Annulation Cascade: A Facile Access to β-Sulfonylated Dibenzobenzo[b,d]azepin-6-ones

  • Mengting Zhang ,
  • Jiayi Jiang ,
  • Zhixin Qiu ,
  • Nianhua Luo ,
  • Jiapian Huang
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  • College of Pharmacy, Gannan Medical University, Ganzhou 341000, China

Received date: 2026-07-16

  Online published: 2026-08-26

Supported by

Fundamental Research Funds for Gannan Medical University (No. QD202429).

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Abstract

The dibenzo[b,d]azepin-6-one scaffold is widely present in natural products and pharmaceutically active molecules, and its efficient construction has long been a research hotspot in organic synthesis. Herein, we report a visible-light-catalyzed radical SO2 insertion/cyclization cascade reaction for the rapid construction of β-sulfonylated dibenzo[b,d]azepin-6-ones. Under visible-light irradiation, using Ir(ppy)₃ as the photocatalyst, aryl diazonium salts, DABCO·(SO2)₂, and N-aryl acrylamide substrates undergo a tandem sulfonylation/annulation process at room temperature to afford a series of target products in moderate to good yields. This protocol features mild conditions and simple operation, along with good functional group compatibility. Mechanistic studies indicate that the reaction proceeds through a radical pathway, involving key steps such as SO2 insertion, radical addition, and intramolecular cyclization. This work provides a convenient and green route for the construction of β-sulfonylated dibenzo[b,d]azepin-6-one frameworks, which holds promise for applications in medicinal chemistry and functional materials. The general procedure for this visible-light-induced radical SO2 insertion/annulation for the synthesis of β-sulfonylated dibenzo[b]azepin-6-ones is as follows: To a mixture of N-aryl acrylamide substrates (0.2 mmol), aryl diazonium salts (0.3 mmol), DABCO·(SO2)₂ (0.3 mmol), Ir(ppy)3 (2 mol%) in a 10 mL Schlenk tube was added acetonitrile (3.0 mL). The vessel was evacuated and backfilled with N2 for three times. The tube was screw-capped and stirred at 35 oC under irradiation of 24V blue LEDs (distance app. 5 cm) for 24h. After completion of the reaction, the mixture was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel using a mixture of petroleum ether and ethyl acetate (VPE:VEA = 3:1) as the eluent to afford the desired products.

Key words： Dibenzobenzo[b,d]azepin-6-ones; SO2 insertion; β-sulfonylated; visible-light-induced; radical cascade cyclization

Cite this article

Mengting Zhang , Jiayi Jiang , Zhixin Qiu , Nianhua Luo , Jiapian Huang . Visible-Light-Induced SO2 Insertion/Annulation Cascade: A Facile Access to β-Sulfonylated Dibenzobenzo[b,d]azepin-6-ones[J]. Acta Chimica Sinica, 0 : 4 -4 . DOI: 10.6023/A26070250

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