Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 16, Issue 24, Pages 4087-4094Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.202100978
Keywords
Anthraquinone; recyclability; CDC-reactions; N-aryl tetrahydroisoquinolines; photocatalysis
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Funding
- National Natural Science Foundation of China [21101085]
- Natural Science Foundation of Liaoning Province [2021-BS-249, LJKZ0373, 2015020196]
- Liaoning Revitalization Talents Program [XLYC1902085]
- PetroChina Innovation Foundation [2018D-5007-0507]
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This study reports the efficient catalytic application of a novel photosensitizer under specific conditions, with good yields and high substrate tolerance, also demonstrating its recyclability and reusability properties.
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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