Energy-transfer-enabled photocatalytic transformations of aryl thianthrenium salts

Aryl thianthrenium salts are valuable in photocatalysis but traditionally require external electron donors for activation. This study introduces an energy transfer (EnT) strategy for the activation of aryl thianthrenium salts using 2,3,4,5,6-penta(carbazol-9-yl)benzonitrile (5CzBN) as a metal-free photocatalyst, eliminating the need for external donors. Utilizing this EnT approach, we achieve C-H deuteration of arenes under visible light with CDCl<sub>3</sub> as a deuterium source to synthesize various deuterated aromatic compounds, including important natural products and pharmaceuticals. Additionally, this strategy enables diverse functionalizations including borylation, arylation, cyanation, and selenylation, enhancing the applicability of aryl sulfonium salts in environmentally friendly photocatalysis.

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Publication Details

Journal
Nature Communications
Published
2024-11-08
DOI
https://doi.org/10.1038/s41467-024-54079-3
Citations
47
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
11.75

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article

Energy-transfer-enabled photocatalytic transformations of aryl thianthrenium salts

Kai Sun, Chang Ge, Bin Yu, Bing Yu et al.
47 citations
Nature Communications
Radical Photochemical Reactions
11.75
article

Energy-transfer-enabled photocatalytic transformations of aryl thianthrenium salts

Kai Sun, Chang Ge, Bin Yu, Bing Yu, Xiaolan Chen, Lingbo Qu
article en
47 citations

Abstract

Aryl thianthrenium salts are valuable in photocatalysis but traditionally require external electron donors for activation. This study introduces an energy transfer (EnT) strategy for the activation of aryl thianthrenium salts using 2,3,4,5,6-penta(carbazol-9-yl)benzonitrile (5CzBN) as a metal-free photocatalyst, eliminating the need for external donors. Utilizing this EnT approach, we achieve C-H deuteration of arenes under visible light with CDCl<sub>3</sub> as a deuterium source to synthesize various deuterated aromatic compounds, including important natural products and pharmaceuticals. Additionally, this strategy enables diverse functionalizations including borylation, arylation, cyanation, and selenylation, enhancing the applicability of aryl sulfonium salts in environmentally friendly photocatalysis.

Nature CommunicationsVol. 15(1)
Zhengzhou University (CN), Zhengzhou Business University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Henan Province, Higher Education Discipline Innovation Project
Affordable and clean energy
Openalex Percentile: Top 1%
Radical Photochemical Reactions
11.75
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Energy-transfer-enabled photocatalytic transformations of aryl thianthrenium salts — Kai Sun, Chang Ge, et al. · Nature Communications (2024) | TGRS Research Map | TGRS