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

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 O2-activation, enabling the facile and atom-economical synthesis of tetra-substituted imi...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 87; no. 15; pp. 10372 - 10376
Main Authors Takeda, Aki, Okai, Hayaki, Watabe, Kyoji, Iida, Hiroki
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.08.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MULTISUBSTITUTED IMIDAZOLES
HETEROCYCLES
ONE-POT SYNTHESIS
1,2,4,5-TETRASUBSTITUTED IMIDAZOLES
AMINES
OXIDATIONS
CHEMISTRY
TETRASUBSTITUTED IMIDAZOLES
INDOLES
C-H
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Summary: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 O2-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.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00596