2-(Trimethylsilyl)-λ3-Phosphinine: synthesis, coordination chemistry, and reactivity

Marija H. Habicht, Friedrich Wossidlo, Tobias Bens, Evgeny A. Pidko, Christian Müller

Research output: Contribution to journalArticleAcademicpeer-review

45 Citations (Scopus)
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Abstract

The [4+2] cycloaddition reaction between 2-pyrone and Me3Si−C≡P gives the corresponding 2-(trimethylsilyl)-λ3-phosphinine in good yields as a rather air and moisture stable, colorless oil. Insight into the regioselectivity of the pericyclic reaction was obtained with the help of deuterium-labeling experiments. The silyl-phosphinine acts as a ligand for the preparation of a Cu(I) and the first crystallographically characterized phosphinine-Ag(I) complex. The title compound was further used as a starting material for an alternative preparation of the parent phosphinine C5H5P by means of protodesilylation with HCl. C5H5P reacts with CuBr⋅S(CH3)2 to give an infinite Cu(I)Br coordination polymer. DFT calculations shed light on the influence of the -Si(CH3)3 group on the electronic properties of the aromatic phosphorus heterocycle.

Original languageEnglish
Pages (from-to)944-952
Number of pages9
JournalChemistry : A European Journal
Volume24
Issue number4
DOIs
Publication statusPublished - 19 Jan 2018
Externally publishedYes

Funding

Financial support by Freie Universität Berlin and the Deutsche Forschungsgemeinschaft (DFG) is gratefully acknowledged. E.A.P. thanks the Ministry of Education and Science of the Russian Federation (Project 11.1706.2017/4.6) for support. We thank Mrs. Antonia Loibl for her help with creating part of the graphical material.

Keywords

  • coordination chemistry
  • heterocycles
  • ligands
  • phosphorus

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