A Bis-Sulfonyl O,C,O Aryl Pincer Ligand and its Tin(II) Complex: Synthesis, Structural Studies, and DFT Calculations

Mohammad El ezzi , Romaric Lenk (1) , David Madec , Jean-Marc Sotiropoulos (2) , Sonia Mallet-Ladeira , Annie Castel (3)

1 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation
2 IPREM - Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux
3 LHFA - Laboratoire Hétérochimie Fondamentale et Appliquée

The efficiency of the deprotonated aryl bis‐sulfone [2,6‐{(p‐tolyl)SO2}2C6H3]− as an O,C,O‐coordinating pincer‐type ligand was described. The bis‐sulfone precursor was synthesized using a straightforward palladium‐catalyzed cross‐coupling reaction. As a result of directed ortho metalation (DoM) through sulfonyl groups, a selective lithiation of the aryl group was achieved and the corresponding carbanion was isolated and its structure determined by single‐crystal X‐ray diffraction analysis. A heteroleptic tin(II) complex has been prepared by a nucleophilic substitution reaction. Crystallographic analysis and DFT calculations indicate that the bis‐sulfonyl moiety acts as a new O,C,O‐coordinating pincer‐type ligand with intramolecular SO coordination to a tin(II) center. The cis form with the two nonbonded oxygen atoms of the sulfonyl groups on the same side is preferentially obtained.

Keywords: carbene homologues density functional calculations NMR spectroscopy pincer ligands tin

Domains: Polymers; Material chemistry; Theoretical and/or physical chemistry; Analytical chemistry

Mohammad El ezzi, Romaric Lenk, David Madec, Jean-Marc Sotiropoulos, Sonia Mallet-Ladeira, et al.. A Bis-Sulfonyl O,C,O Aryl Pincer Ligand and its Tin(II) Complex: Synthesis, Structural Studies, and DFT Calculations. Angewandte Chemie International Edition, 2015, 54 (3), pp.805-808. ⟨10.1002/anie.201406283⟩. ⟨hal-02320620⟩