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Issue 22, 2016
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Applications of N-heterocyclic imines in main group chemistry

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Abstract

The imidazolin-2-imino group is an N-heterocyclic imino functionality that derives from the class of compounds known as guanidines. The exocyclic nitrogen atom preferably bonds to electrophiles and its electron-donating character is markedly enhanced by efficient delocalization of cationic charge density into the five-membered imidazoline ring. Thus, this imino group is an excellent choice for thermodynamic stabilization of electron-deficient species. Due to the variety of available imidazoline-based precursors to this ligand, its steric demand can be tailored to meet the requirements for kinetic stabilization of otherwise highly reactive species. Consequently, it does not come as a surprise that the imidazolin-2-iminato ligand has found widespread applications in transition-metal chemistry to furnish pincer complexes or “pogo stick” type compounds. In comparison, the field of main-group metal compounds of this ligand is still in its infancy; however, it has received growing attention in recent years. A considerable number of electron-poor main-group element species have been described today which are stabilized by N-heterocyclic iminato ligands. These include low-valent metal cations and species that are marked by formerly unknown bonding modes. In this article we provide an overview on the present chemistry of main-group element compounds of the imidazolin-2-iminato ligand, as well as selected examples for the related imidazolidin- and benzimidazolin-2-imino system.

Graphical abstract: Applications of N-heterocyclic imines in main group chemistry

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Publication details

The article was received on 29 Feb 2016 and first published on 08 Aug 2016


Article type: Review Article
DOI: 10.1039/C6CS00163G
Citation: Chem. Soc. Rev., 2016,45, 6327-6344
  • Open access: Creative Commons BY license
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    Applications of N-heterocyclic imines in main group chemistry

    T. Ochiai, D. Franz and S. Inoue, Chem. Soc. Rev., 2016, 45, 6327
    DOI: 10.1039/C6CS00163G

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