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Synlett
DOI: 10.1055/a-2705-9158
Letter

Light-Induced, Iron-Promoted Formation of Benzotetraphenones via Paternò–Büchi Photorearrangement/Electrocyclization: A Route to Polyaromatic Scaffolds

Authors

  • Ícaro Antônio Oliveira Bozzi

    1   Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil

  • Dandara dos Santos Borges

    1   Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil

  • Bruno Dival

    1   Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil

  • Willian Xerxes Coelho Oliveira

    1   Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil

  • Luana Alves Machado

    1   Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil

  • Renata Gomes Almeida

    1   Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil

  • Maria Helena Araujo

    2   Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil (Ringgold ID: RIN28114)

  • Edmond Gravel

    3   DRF/Joliot/DMTS/SCBM, CEA, Gif-sur-Yvette, France

  • Eufrânio Nunes da Silva Júnior

    4   Química, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil

  • Guilherme Augusto Jardim 

    1   Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil

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
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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.



Publication History

Received: 15 July 2025

Accepted after revision: 01 September 2025

Accepted Manuscript online:
19 September 2025

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