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Synthesis, structure, and stability of a set of C-stereogenic heteroditopic P, S ligands☆

Mammadova, Aynura
Kargin, Denis
Bruhn, Clemens
Pietschnig, Rudolf

This study focuses on synthesis and investigation of coordination modes of phosphorus and sulfur-containing C-stereogenic compounds, prepared from thioanisole. Isolation of the C-stereogenic organolithium compound [RR'CHLi2THF]₂ (R = C₆H₅S, R’ = (CH₃)₃Si, THF = tetrahydrofuran) instead of in situ usage turned out to be mandatory for controlled reactivity. Variation of the steric and electronic properties of the substituents at phosphorus furnished three different phosphane substituted P, S ligands RR'CHPPh₂, RR'CHP(N(C₂H₅)₂)₂, and RR'CHP(t-C₄H₉)₂. Furthermore, the corresponding chalcogenphosphoranes were synthesized by oxidation with elemental sulfur and selenium. Preliminary investigation of the coordination behavior of RR'CHP(t-C₄H₉)₂, RR'CHP(S)(t-C₄H₉)₂ and RR'CHP(Se)(t-C₄H₉)₂ towards coinage metals was explored with Au(tht)Cl, both for the phosphanes and the corresponding phosphoranes. Intermolecular aurophilic interactions have been observed for the selenophosphorane exclusively.

Sponsor
Gefördert im Rahmen des Projekts DEAL
Citation
In: Journal of Organometallic Chemistry Volume 1011 / Issue May (2024-03-30) , S. ; eissn:1872-8561
Collections
@article{doi:10.17170/kobra-2024080710643,
  author    ={Mammadova, Aynura and Kargin, Denis and Bruhn, Clemens and Pietschnig, Rudolf},
  title    ={Synthesis, structure, and stability of a set of C-stereogenic heteroditopic P, S ligands☆},
  keywords ={540 and Phosphor and Schwefel and Komplexbildungsreaktion and Goldkomplexe and Lithiumorganische Verbindungen and Chiralität },
  copyright  ={http://creativecommons.org/licenses/by/4.0/},
  language ={en},
  journal  ={Journal of Organometallic Chemistry},
  year   ={2024-03-30}
}