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Synthesis of (2-hydroxyphenyl)(fusedphenyl)methanones via the photo-induced rearrangement of 2′-arylisoflavones

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Abstract

The photo-induced rearrangement of 2′-arylisoflavones (aryl = phenyl, furyl, 3-pyridyl, 1-naphenyl, and 2-naphenyl) for the synthesis of (2-hydroxyphenyl)(fused phenyl)methanones in EtOH under an Ar atmosphere at room temperature has been developed. The described method proceeded smoothly without requiring any transition metal catalyst, oxidant, or additives. Moreover, using ethanol as the solvent is not only cost efficient but also environmentally friendly. Further treatment of methanone analogues with AlCl3 yielded highly conjugated polycyclic aromatic hydrocarbon (PAH) derivatives.

Graphical abstract: Synthesis of (2-hydroxyphenyl)(fusedphenyl)methanones via the photo-induced rearrangement of 2′-arylisoflavones

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Publication details

The article was received on 08 Nov 2018, accepted on 21 Dec 2018 and first published on 22 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02779J
Citation: Org. Biomol. Chem., 2019, Advance Article
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    Synthesis of (2-hydroxyphenyl)(fusedphenyl)methanones via the photo-induced rearrangement of 2′-arylisoflavones

    P. Wang, J. Zhang, T. Wang, Y. Liang and Z. Zhang, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C8OB02779J

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