Cross-dehydrogenative Coupling of N-Aryl Tetrahydroisoquinolines Catalyzed by an Anthraquinone-containing Polymeric Photosensitizer |
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Authors: | Fei Wang Dan Yu Yang Chen Jing Sun Jing-Yun Wang Prof. Ming-Dong Zhou |
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Affiliation: | School of Petrochemical Engineering, Liaoning Petrochemical University, 113001 Dan Dong Road 1, Fushun, P. R. China |
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Abstract: | This work reports the photocatalytic application of an anthraquinone-containing polymeric photosensitizer (AQ-PHEMA) in the visible light-induced cross - dehydrogenative-coupling of N-aryl tetrahydroisoquinolines with several nucleophiles, including nitromethane, 1-methyl-2-alkyl ketone and dialkyl (aryl) phosphine oxide. The results revealed that the reaction could be catalyzed by AQ-PHEMA efficiently to afford a series of 1-substituted-2-aryl-1,2,3,4-tetrahydroisoquinolines in good to excellent yields with nice substrate tolerance under aerobic conditions at room temperature. The practical application potential was also showcased by a gram-scale synthesis. More importantly, the utilization of AQ-PHEMA as a heterogeneous photosensitizer also showed nice recyclability and reusability of the catalyst, whereas AQ-PHEMA can be easily separated and reused for at least 8 times without significant loss of photocatalytic activity. |
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Keywords: | Anthraquinone recyclability CDC-reactions N-aryl tetrahydroisoquinolines photocatalysis |
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