1. A One‐Pot Approach for Bio‐Based Arylamines via a Combined Photooxidative Dearomatization‐Rearomatization Strategy.
- Author
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Afanasenko, Anastasiia, Kavun, Aleksei, Thomas, Dylan, and Li, Chao‐Jun
- Subjects
AROMATIC amines ,AZINES ,HAZARDOUS wastes ,CHEMICAL industry ,RENEWABLE natural resources ,NATURAL products ,PHENOLS - Abstract
The synthesis of arylamines from renewable resources under mild reaction conditions is highly desired for the sustainability of the chemical industry, where the production of hazardous waste is a prime concern. However, to date, there are very few tools in chemists' toolboxes that are able to produce arylamines in a sustainable manner. Herein, a robust one‐pot approach for constructing bio‐based arylamines via a combined photooxidative dearomatization‐rearomatization strategy is presented. The developed methodology enables the synthesis of structurally complex amines in moderate‐to‐good isolated yields using biomass‐derived phenols, natural α‐amino acids, and naphthols under remarkably mild reaction conditions. For the photooxygenation of phenols, a novel chrysazine‐based catalyst system was introduced, demonstrating its efficiency for the synthesis of natural products – hallerone, rengyolone, and the pharmaceutically relevant prodrug DHED. [ABSTRACT FROM AUTHOR]
- Published
- 2022
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