Electrochemically promoted diamidation of alkenes to dihydroimidazole skeleton

The dihydroimidazole framework is a valuable heterocyclic compound widely found in natural products, ligands, molecular catalysts, pesticides, etc. The construction of a dihydroimidazole framework from alkenes is an attractive synthesis approach. Herein, we report a simple and environmentally friend...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2024-01, Vol.11 (24), p.7147-7152
Main Authors: Guo-Ao, Wang, Kai-Wei, Chen, Yu-Da, Huang, Yu-Yuan, Zhang, Xiu-Jin Meng, Fei-Hu, Cui, Ying-Ming, Pan, Hai-Tao Tang
Format: Article
Language:English
Subjects:
Alkenes
Catalysts
Chemical synthesis
Diamines
Electrochemistry
Heterocyclic compounds
Natural products
Oxidants
Oxidizing agents
Pesticides
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Summary:The dihydroimidazole framework is a valuable heterocyclic compound widely found in natural products, ligands, molecular catalysts, pesticides, etc. The construction of a dihydroimidazole framework from alkenes is an attractive synthesis approach. Herein, we report a simple and environmentally friendly electrocatalytic diamination reaction of alkenes. The reaction involves constructing a dihydroimidazole framework from readily available alkenes, CH3CN, and H2O. CH3CN serves as a solvent and a nitrogen source, whereas H2O provides an oxygen source without the need for catalysts and oxidants. The synthesized 3,4-dihydroimidazole compound can be further hydrolyzed into vicinal diamines. As far as we know, the synthesis of dihydroimidazole frameworks through electrochemical Ritter-type diamination of alkenes has not been reported yet.
ISSN:2052-4110
2052-4110
DOI:10.1039/d4qo01445f