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<i>N</i>-Metallocenyl Ynamides: Preparation, Reactivity, and Synthesis of <i>ansa</i>[3]-Ferrocenylamides


Mahe, Capucine; Blacque, Olivier; Gasser, Gilles; Gandon, Vincent; Cariou, Kevin (2023). <i>N</i>-Metallocenyl Ynamides: Preparation, Reactivity, and Synthesis of <i>ansa</i>[3]-Ferrocenylamides. Organic Letters, 25(4):624-629.

Abstract

The first synthesis of various N-metallocenyl ynamides has been developed, and two strategies for the oxidative cyclization of N-ferrocenyl ynamide into ansa[3]-ferrocenylamide are also reported. The mechanism for the iodine(III)-triggered transformation has been studied by means of DFT calculations, showing that it proceeds through a concerted iodination deprotonation step.

Abstract

The first synthesis of various N-metallocenyl ynamides has been developed, and two strategies for the oxidative cyclization of N-ferrocenyl ynamide into ansa[3]-ferrocenylamide are also reported. The mechanism for the iodine(III)-triggered transformation has been studied by means of DFT calculations, showing that it proceeds through a concerted iodination deprotonation step.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Life Sciences > Biochemistry
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Uncontrolled Keywords:Organic Chemistry, Physical and Theoretical Chemistry, Biochemistry
Language:English
Date:3 February 2023
Deposited On:19 Jan 2024 14:32
Last Modified:30 Jun 2024 01:37
Publisher:American Chemical Society (ACS)
ISSN:1523-7052
OA Status:Closed
Publisher DOI:https://doi.org/10.1021/acs.orglett.2c04169
PubMed ID:36688847
Project Information:
  • : FunderUniversit? Paris-Saclay
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  • : FunderCentre National de la Recherche Scientifique
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  • : FunderChimie ParisTech, PSL University
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  • : FunderEcole Polytechnique
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