Copper‐Catalyzed Heterocyclic Recombination of Aziridine and Diazetidine for the Synthesis of Imidazolidine**
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- 23 June 2023
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 29 (43) , e202301071
Abstract
The discovery of new catalytic applications for metals remains an important goal in organic synthesis. If a catalyst has multiple functions, such as inducing bond cleavage and formation, it can streamline multi‐step transformations. Herein, the Cu‐catalyzed synthesis of imidazolidine through heterocyclic recombination between aziridine and diazetidine is reported. Mechanistically, Cu catalyzes the conversion of diazetidine into the corresponding imine, which then reacts with aziridine to form imidazolidine. The scope is sufficiently wide to form various imidazolidines, as many functional groups are compatible with the reaction conditions.Keywords
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Funding Information
- Precursory Research for Embryonic Science and Technology (JPMJPR20D8)
This publication has 56 references indexed in Scilit:
- Cu(I)-Catalyzed Diamination of Conjugated Dienes. Complementary Regioselectivity from Two Distinct Mechanistic Pathways Involving Cu(II) and Cu(III) SpeciesJournal of the American Chemical Society, 2011
- AgSbF6-Promoted Cycloaddition Reaction of 2-Trifluoromethyl-N-tosylaziridine with AldehydesOrganic Letters, 2011
- Palladium-Catalyzed Insertion of CO2 into Vinylaziridines: New Route to 5-VinyloxazolidinonesOrganic Letters, 2011
- Cu(I)-Catalyzed Regioselective Diamination of Conjugated Dienes via Dual Mechanistic PathwaysJournal of the American Chemical Society, 2010
- New Diimine−Copper Complexes: An Efficient and Simple Catalyst System for Buchwald N-Arylation of IndoleOrganometallics, 2008
- N,N‘-Ditosylhydrazine: A Convenient Reagent for Facile Synthesis of DiazoacetatesOrganic Letters, 2007
- Dynamic Kinetic Asymmetric Cycloadditions of Isocyanates to VinylaziridinesJournal of the American Chemical Society, 2003
- Short and Efficient Synthesis of Optically Active N-Tosyl Aziridines from 2-Amino AlcoholsMolecules, 2002
- Copper-Catalyzed Nitrogen Transfer Mediated by Iodosylbenzene PhIOJournal of the American Chemical Society, 2001
- Bromine-Catalyzed Aziridination of Olefins. A Rare Example of Atom-Transfer Redox Catalysis by a Main Group ElementJournal of the American Chemical Society, 1998