Abstract
The electrophilic amination of functionalized organocopper and organozinc reagents by N,N-dialkyl-O-benzoyl hydroxylamine derivatives to provide functionalized tertiary aryl amines has been accomplished efficiently at ambient temperature using in situ generated Fe(0) nanoparticles from Fe(acac)3. The formation and role of Fe(0)-nanoparticles were investigated. The mechanism involving Feassisted nucleophilic displacement at the nitrogen centre of the hydroxylamine derivative by the Cu/Zn-reagents is described. The organo- copper/zinc reagents are readily prepared by the treatment of the corresponding Grignard reagents with CuI and ZnCl2 respectively.
Keywords: Electrophilic amination, Tertiary aryl amines, Organocopper reagent, Organozinc reagent, Iron(0) nanoparticles
Current Organic Chemistry
Title:Iron Nanoparticles-Catalyzed Electrophilic Amination of Functionalized Organocopper and Organozinc Reagents
Volume: 16 Issue: 11
Author(s): Sukalyan Bhadra, Sabir Ahammed and Brindaban C. Ranu
Affiliation:
Keywords: Electrophilic amination, Tertiary aryl amines, Organocopper reagent, Organozinc reagent, Iron(0) nanoparticles
Abstract: The electrophilic amination of functionalized organocopper and organozinc reagents by N,N-dialkyl-O-benzoyl hydroxylamine derivatives to provide functionalized tertiary aryl amines has been accomplished efficiently at ambient temperature using in situ generated Fe(0) nanoparticles from Fe(acac)3. The formation and role of Fe(0)-nanoparticles were investigated. The mechanism involving Feassisted nucleophilic displacement at the nitrogen centre of the hydroxylamine derivative by the Cu/Zn-reagents is described. The organo- copper/zinc reagents are readily prepared by the treatment of the corresponding Grignard reagents with CuI and ZnCl2 respectively.
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Cite this article as:
Bhadra Sukalyan, Ahammed Sabir and C. Ranu Brindaban, Iron Nanoparticles-Catalyzed Electrophilic Amination of Functionalized Organocopper and Organozinc Reagents, Current Organic Chemistry 2012; 16 (11) . https://dx.doi.org/10.2174/138527212800672646
DOI https://dx.doi.org/10.2174/138527212800672646 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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