Modification of a common β-diketiminate NacNac framework via sequential lithiation and small molecule insertion

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Abstract

A widely utilised class of ligands in synthesis and catalysis, β-diketiminate (BDI) or NacNac compounds were initially considered innocent in the sense that they remained intact in all their applications. That changed when the γ-C−H unit of their NCCCN backbone was found to engage in reactions with electrophiles. Here, we show that this special reactivity can be used advantageously to prepare tripodal modifications of the common NacNac ligand derived from 2,6-diisopropylphenyl-β-methyldiketimine [NacNacH (Me, Dipp)]. Lithiation to give NacNacLi, followed by reactions with isocyanates, isothiocyanates and a carbodiimide, have afforded a series of tripodal NacNac variants having N,N,N,O; N,N,N,S; or N,N,N,N potential dentation sites, many of which have been crystallographically characterised. Distinct ligating modes of these new ligands have been elucidated through the crystal structures of their lithiated derivatives.
Original languageEnglish
Article numbere202303373
Number of pages11
JournalChemistry - A European Journal
Volume30
Issue number15
Early online date30 Nov 2023
DOIs
Publication statusPublished - 12 Mar 2024

Keywords

  • small molecule insertion
  • NacNac ligand
  • NacNac molecules
  • ligand synthesis
  • lithium

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