Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 15, Pages 10372-10376Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00596
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Funding
- JSPS/MEXT KAKENHI [19K05617]
- Society of Iodine Science
- Shimane University Internal Competitive Grants
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In this study, the oxidative cross-dehydrogenative coupling reaction between amidines and chalcones catalyzed by flavin and iodine was demonstrated. The riboflavin-iodine catalytic system played multiple roles in substrate and O-2 activation, enabling the facile and atom-economical synthesis of tetra substituted imidazoles in good yields (60-87%). This metal-free reaction consumed only 1 equiv of molecular oxygen and generated 2 equiv of environmentally benign H2O as the only byproduct.
Herein, we demonstrated the oxidative cross-dehydrogenative coupling between amidines and chalcones catalyzed by flavin and iodine. The riboflavin-iodine catalytic system played multiple roles in substrate-and O-2-activation, enabling the facile and atom-economical synthesis of tetra substituted imidazoles in good yields (60-87%). This metal-free reaction consumed only 1 equiv of molecular oxygen and generated 2 equiv of environmentally benign H2O as the only byproduct.
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