Skip to Main content Skip to Navigation
Theses

Synthèses de biaryles atropoenrichis et de biphénylènes via des arynes substitués

Abstract : This work consisted in the study of the “aryne coupling”, a transition-metal free process to access biaryl moieties, which involves the reaction between two in situ generated intermediates: a nucleophilic aryllithium derivative and an electrophilic aryne. This work resided in the optimization of the atropoenantioselective version of the aryne coupling and its application to the formal synthesis of (-)-steganacin. We then moved to the atropoenantioselective version of the reaction, by introducing chiral ligands in the reaction mixture, which aim was to coordinate the aryllithium species and to transfer their chiral information to the biaryl axis. After optimization of various reaction parameters, some enantiomeric excesses were obtained as well as various side products in some cases, among which biphenylene derivatives. According to the potential applications of these compounds, another part of this work was dedicated to their synthesis by means of aryne dimerization reactions.
Document type :
Theses
Complete list of metadatas

Cited literature [709 references]  Display  Hide  Download

https://tel.archives-ouvertes.fr/tel-02336228
Contributor : Abes Star :  Contact
Submitted on : Monday, October 28, 2019 - 4:58:33 PM
Last modification on : Tuesday, October 29, 2019 - 1:35:18 AM
Long-term archiving on: : Wednesday, January 29, 2020 - 6:07:55 PM

File

Augros_David_2018_ED222.pdf
Version validated by the jury (STAR)

Identifiers

  • HAL Id : tel-02336228, version 1

Collections

Citation

David Augros. Synthèses de biaryles atropoenrichis et de biphénylènes via des arynes substitués. Chimie organique. Université de Strasbourg, 2018. Français. ⟨NNT : 2018STRAF040⟩. ⟨tel-02336228⟩

Share

Metrics

Record views

179

Files downloads

96