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Synlett
DOI: 10.1055/a-2705-9158
DOI: 10.1055/a-2705-9158
Letter
Published as part of the Special Topic Alkynes in Organic Synthesis
Light-Induced, Iron-Promoted Formation of Benzotetraphenones via Paternò–Büchi Photorearrangement/Electrocyclization: A Route to Polyaromatic Scaffolds
Authors
Supported by: Coordenação de Aperfeiçoamento de Pessoal de Nível Superior COFECUB project No. 88881.878986/2023-01,PROBAL-DAAD 88881.986162/2024-01
Supported by: Conselho Nacional de Desenvolvimento Científico e Tecnológico 151294/2022-4,200115/2022-7,405052/2021-9,421655/2023-2,441404/2023-5,PQ 309774/2020-9
Supported by: Fundação de Amparo à Pesquisa do Estado de Minas Gerais APQ-00724-23,APQ-01538-24,APQ-04401-23,BPD-00659-22,TEC-RED-00081-23
Funding Information GAMJ, MHA, and ENSJ are supported by FAPEMIG grants APQ-01538-24, APQ-02496-24, APQ-04401-23, APQ-00724-23, and TEC-RED-00081-23 and CNPq grants 301881-2025-1, 403579-2024-4, 441404/2023-5, 421655/2023-2, 151294/2022-4, and 200115/2022-7. Special thanks to CAPES PROBAL-DAAD 88881.986162/2024-0 and CAPES-COFECUB project No. 88881.878986/2023-01. RGA thanks BPD-00659-22. LAM thanks 151734-2024-0 and 402980-2024-7.
Abstract
We report a light-induced, iron-promoted method for the synthesis of polyaromatic benzotetraphenone derivatives via a tandem [2+2] Paternò–Büchi photorearrangement/electrocyclization pathway. Irradiation of anthraquinone with diphenylacetylenes under 370 nm LED light in the presence of FeCl₃ afforded novel polyaromatic scaffolds in excellent yields. The structures of the products were confirmed by single-crystal X-ray diffraction, revealing planar, rigid frameworks with promising photophysical properties. This strategy offers a new platform for constructing highly conjugated, luminescent molecules from simple precursors under mild conditions.
Keywords
Photochemistry - Photorearrangement - Paternò–Büchi - Lewis acid catalysis - BenzotetraphenonesPublication History
Received: 15 July 2025
Accepted after revision: 01 September 2025
Accepted Manuscript online:
19 September 2025
Article published online:
27 November 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
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