4.7 Article

Metal-Free Atom-Economical Synthesis of Tetra-Substituted Imidazoles via Flavin-Iodine Catalyzed Aerobic Cross-Dehydrogenative Coupling of Amidines and Chalcones

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JOURNAL OF ORGANIC CHEMISTRY
卷 87, 期 15, 页码 10372-10376

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00596

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  1. JSPS/MEXT KAKENHI [19K05617]
  2. Society of Iodine Science
  3. 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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