Reactions of substituted arynes and diphenylphosphine oxide or diphenylphosphine-borane complex toward dibenzophospholes – impact of aryne substituents

Abstract

The reaction of diphenylphosphine oxide successively with two aryne precursors was investigated in order to access valuable functionalizable nonsymmetrical dibenzophospholes. The reactions proved sensitive to substituents of aryne precursors able to coordinate the incoming lithiated nucleophile.

Graphical Abstract

Keywords:

• Arynes
• organolithiums
• secondary phosphine oxides
• secondary phosphine-borane complexes
• dibenzophospholes
• halogen/metal exchange

Acknowledgements

The CNRS, the Université de Strasbourg and the GDR Phosphore are kindly acknowledged for their support. The authors thank Dr. Angela Marinetti and Dr. Arnaud Voituriez for discussions. The authors also thank Dr Emeric Wasielewski (NMR platform) and Matthieu Chessé (analytical facilities) of the LIMA (UMR7042 CNRS-Unistra-UHA), as well as the analytical facilities of the Fédération de Chimie “Le Bel” (FR2010) of the Université de Strasbourg, who contributed, by their valuable technical and scientific support, to the achievement of this research project.

Disclosure statement

The authors declare no conflict of interest.

Additional information

Funding

This work was funded by the French Agence Nationale de la Recherche (ANR), grant number ANR-15-CE29-0012-02 (HelPhos).