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Gold-Catalyzed One-Pot Synthesis of Polyfluoroalkylated Oxazoles from N-Propargylamides Under Visible-Light Irradiation |
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| Authors: | Yantao Liu Yating Shi Lanen Wei Ke Zhao Dr. Jingjing Zhao Prof. Puyu Zhang Prof. Xuejun Xu Prof. Pan Li |
| Affiliation: | 1. Department Institute of Functional Organic Molecular Engineering, College of Chemistry and Chemical Engineering, Henan University, Kaifeng, 475004 P. R. China These authors contributed equally.;2. Department Institute of Functional Organic Molecular Engineering, College of Chemistry and Chemical Engineering, Henan University, Kaifeng, 475004 P. R. China |
| Abstract: | A gold-catalyzed synthesis of polyfluoroalkylated oxazoles from N-propargylamides under visible-light irradiation has been developed. These reactions display excellent compatibility of radicals and gold catalysts under visible-light irradiation. Mechanistic experiments indicate that polyfluoroalkyl iodides play a dual role in enhanced compatibility of radicals and gold catalysts through assisted protodeauration of vinyl gold and reactivated the gold catalyst. In addition, PPh3AuNTf2 not only activates N-propargylamide to generate vinyl gold intermediate, but also greatly promotes homolysis of polyfluoroalkyl iodides under blue light irradiation. |
| Keywords: | Visible-Light Gold catalysis Polyfluoroalkylation N-Propargylamide Oxazole |