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A Bis‐Sulfonyl O,C,O Aryl Pincer Ligand and its Tin(II) Complex: Synthesis, Structural Studies, and DFT Calculations
Author(s) -
El Ezzi Mohammad,
Lenk Romaric,
Madec David,
Sotiropoulos JeanMarc,
MalletLadeira Sonia,
Castel Annie
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201406283
Subject(s) - chemistry , sulfonyl , sulfone , aryl , pincer movement , deprotonation , carbanion , metalation , moiety , ligand (biochemistry) , medicinal chemistry , intramolecular force , sulfoxide , tin , transmetalation , pincer ligand , stereochemistry , polymer chemistry , catalysis , organic chemistry , ion , biochemistry , alkyl , receptor
The efficiency of the deprotonated aryl bis‐sulfone [2,6‐{( p ‐tolyl)SO 2 } 2 C 6 H 3 ] − 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 SO 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.