Skip to Main content Skip to Navigation
Theses

Fonctionnalisation d’énamides par voie radicalaire : Catalyse au fer ou application de la chimie des xanthates

Abstract : The aim of the thesis is to study the addition of radical species on non-aromatic enamide scaffolds in order to access high molecular diversity of cyclic and acyclic nitrogen-containing compounds in a restricted number of steps via sustainable eco-friendly regio- and diastereoselective reactions.Firstly, non-aromatic enamides bearing different functional groups have been synthesized. Then a regio- and diastereoselective iron-catalyzed oxyazidation of enamides was developed in the presence of novel azidobenziodoxolones (ABX) derivatives under mild reaction conditions. In addition, the versatility of the trans α-azido β-esters piperidines was highlighted by the synthesis of various original nitrogen-containing polycycles.Subsequently, C3 alkylation of enamides with α-halogenocarbonyles. was carried out through an iron (II)-catalysis or a metallic iron-mediated process.Finally, radical xanthate chemistry was applied to achieve the metal-free alkylation of the C3 position of enamides or the difunctionalization of enamides in the presence of a nucleophile
Complete list of metadatas

Cited literature [227 references]  Display  Hide  Download

https://tel.archives-ouvertes.fr/tel-02491782
Contributor : Abes Star :  Contact
Submitted on : Wednesday, February 26, 2020 - 1:15:13 PM
Last modification on : Thursday, February 27, 2020 - 1:55:09 AM

File

sylvain-bertho_3374.pdf
Version validated by the jury (STAR)

Identifiers

  • HAL Id : tel-02491782, version 1

Collections

Citation

Sylvain Bertho. Fonctionnalisation d’énamides par voie radicalaire : Catalyse au fer ou application de la chimie des xanthates. Chimie organique. Université d'Orléans, 2018. Français. ⟨NNT : 2018ORLE2060⟩. ⟨tel-02491782⟩

Share

Metrics

Record views

63

Files downloads

12