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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
External Photocatalyst-Free C─H Arylation of Aminoquinones Through a Photo-SN1 Pathway
Anam Nawaz1, Jiashen Yang1, Shaozhong Wang1
1State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry, Nanjing University, Nanjing, Jiangsu, China.
Abstract:
We report a visible-light-driven C─H arylation of aminoquinones that proceeds through an external photocatalyst-free, photo-SN1 mechanism, wherein the key phenyl cation intermediates are generated in situ from commercially available anilines. This approach enables direct coupling with various aminoquinones under mild conditions. Mechanistic investigations support an ionic photo-SN1 pathway over a radical manifold, with evidence suggesting that energy transfer from the excited state of the aminoquinone to the diazonium salt facilitates the formation of triplet phenyl cations, which serve as the reactive intermediates in the arylation process.
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