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Perylenequinonoid-catalyzed photoredox activation for the direct arylation of (het)arenes with sunlight

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Abstract

Naturally occurring perylenequinonoid pigments (PQPs) have attracted considerable attention owing to their excellent properties of photosensitization. They have been widely investigated as an aspect of photophysics and photobiology. However, their applications in photocatalysis are yet to be explored. We report here that sunlight along with 1 mol% cercosporin, which is one of the perylenequinonoid pigments, catalyzes the direct C–H bond arylation of (het)arenes by a photoredox process with good regioselectivity and broad functional group compatibility. Furthermore, a gram-scale reaction with great conversions of substrates was achieved even by a cercosporin-containing supernatant without organic solvent extraction and purification after liquid fermentation. Thus we set up a bridge between microbial fermentation and organic photocatalysis for chemical reactions in a sustainable, environmentally friendly manner.

Graphical abstract: Perylenequinonoid-catalyzed photoredox activation for the direct arylation of (het)arenes with sunlight

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Publication details

The article was received on 27 Mar 2019, accepted on 09 Apr 2019 and first published on 09 Apr 2019


Article type: Paper
DOI: 10.1039/C9OB00659A
Citation: Org. Biomol. Chem., 2019, Advance Article

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    Perylenequinonoid-catalyzed photoredox activation for the direct arylation of (het)arenes with sunlight

    S. Zhang, Z. Tang, W. Bao, J. Li, B. Guo, S. Huang, Y. Zhang and Y. Rao, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB00659A

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