A One-Pot Approach for Bio-Based Arylamines via a Combined Photooxidative Dearomatization-Rearomatization Strategy |
| |
Authors: | Dr Anastasiia Afanasenko Aleksei Kavun Dylan Thomas Prof?Dr Chao-Jun Li |
| |
Institution: | Department of Chemistry and, FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke St. W., Montreal, Quebec, H3A 0B8 Canada |
| |
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. |
| |
Keywords: | arylamines dearomatization-rearomatization phenol-amine coupling photooxidation singlet oxygen |
|
|