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

12 December 2022, Version 3
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

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 transfor-mation has been studied by means of DFT calculations, showing that it proceeds through a Concerted Iodination Deprotona-tion step.

Keywords

Ansa-Ferrocenes
Bioorganometallic Chemistry
DFT
Hypervalent Iodine
Metallocenes
Ynamides

Supplementary materials

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Supporting information
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Experimental procedures, optimization tables, NMR spectra, detailed DFT calculations, crystallographic data
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compiund 12e
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compound 12d
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Now Published

N-Metallocenyl Ynamides: Preparation, Reactivity, and Synthesis of ansa[3]-Ferrocenylamides [opens in a new tab]
Capucine Mahe, Olivier Blacque, Gilles Gasser, Vincent Gandon, Kevin Cariou journal article
Organic Letters , Volume 25, Issue 4
Online publication date: Jan 23, 2023

Version History

Dec 12, 2022 Version 3

Version Notes

We added a new section about an original method to access ferrocenophanes from N-ferrocenyl-ynamides. This new reaction relies on a nitrone as the oxygen donor using HFIP as the solvent.

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License

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2022-3fh1t-v3
D O I: 10.26434/chemrxiv-2022-3fh1t-v3 [opens in a new tab]

Funding

European Research Council
GA 681679
Agence Nationale de la Recherche
ANR-10-IDEX-0001-02 PSL

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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