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Literature DB >> 18473463

A Cu(I)-catalyzed C-H alpha-amination of esters. Direct synthesis of hydantoins.

Abstract

This paper describes a novel intermolecular alpha-amination process of esters using CuCl as catalyst and di-tert-butyldiaziridinone as nitrogen source. A variety of hydantoins can be formed effectively under mild reaction conditions.

Entities: Chemical

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Year: 2008 PMID： 18473463 DOI： 10.1021/ja802242h

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

11 in total

Review 1. Cross-Coupling of Heteroatomic Electrophiles.

Authors: Katerina M Korch; Donald A Watson
Journal: Chem Rev Date: 2019-06-11 Impact factor: 60.622

2. Stereoselective radical amination of electron-deficient C(sp3)-H bonds by Co(II)-based metalloradical catalysis: direct synthesis of α-amino acid derivatives via α-C-H amination.

Authors: Hongjian Lu; Yang Hu; Huiling Jiang; Lukasz Wojtas; X Peter Zhang
Journal: Org Lett Date: 2012-09-21 Impact factor: 6.005

3. Metal-catalysed 1,2-diamination reactions.

Authors: Francesca Cardona; Andrea Goti
Journal: Nat Chem Date: 2009-06-22 Impact factor: 24.427

4. Mechanistic Studies on the Synthesis of Pyrrolidines and Piperidines via Copper-Catalyzed Intramolecular C-H Amination.

Authors: José María Muñoz-Molina; Daniel Bafaluy; Ignacio Funes-Ardoiz; Adiran de Aguirre; Feliu Maseras; Tomás R Belderrain; Pedro J Pérez; Kilian Muñiz
Journal: Organometallics Date: 2022-04-29 Impact factor: 3.837

A Cu(I)-catalyzed C-H alpha-amination of esters. Direct synthesis of hydantoins.

Review 1. Cross-Coupling of Heteroatomic Electrophiles.

2. Stereoselective radical amination of electron-deficient C(sp3)-H bonds by Co(II)-based metalloradical catalysis: direct synthesis of α-amino acid derivatives via α-C-H amination.

3. Metal-catalysed 1,2-diamination reactions.

4. Mechanistic Studies on the Synthesis of Pyrrolidines and Piperidines via Copper-Catalyzed Intramolecular C-H Amination.

5. Cu(I)-catalyzed C-H alpha-amination of aryl ketones: direct synthesis of imidazolinones.

6. Cu(I)-catalyzed diamination of disubstituted terminal olefins: an approach to potent NK1 antagonist.

7. Synthesis and activity of novel acylthiourea with hydantoin.

8. Catalytic diamination of olefins via N-N bond activation.

9. Copper-catalyzed diamination of unactivated alkenes with hydroxylamines.

10. Cu-catalyzed N-3-Arylation of Hydantoins Using Diaryliodonium Salts.