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Synthesis 2014; 46(14): 1886-1900
DOI: 10.1055/s-0033-1339127
DOI: 10.1055/s-0033-1339127
special topic
Formation of Imidazolidine-benzothiazole–Copper(II) Complexes via a Copper-Mediated Room-Temperature C–H Activation of Imidazolidinecarbothioamides
Further Information
Publication History
Received: 12 April 2014
Accepted after revision: 05 May 2014
Publication Date:
22 May 2014 (online)
Abstract
Treatment of N-aryl-2-(arylimino)imidazolidine-1-carbothioamide, and unsymmetrical thiourea, with copper(II) chloride or bromide results in aryl sp2 C–H activation (C–S bond formation) at room temperature to form a 2-[2-(arylimino)imidazolidin-1-yl]benzothiazole with concurrent formation of a 2-imidazolidin-1-ylbenzothiazole–copper(II) complex. In all the complexes the imine and benzothiazole nitrogens are s-cis, whereas in the isolated ligands they are s-trans oriented. Due to the presence of a suitable H-donor site and halogen atoms in the metal complexes and ligands, several supramolecular assemblies exist through H-bonding interactions; classical N–H···X–Cu (F, Cl, Br), nonclassical C–H···X–Cu H–bonds, and halogen···π and halogen···halogen interactions.
Key words
copper catalysis - imidazolidinecarbothioamide - C–H activation - aminothiazole - halogen bonding - supramolecular assemblySupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084. Included are X-ray crystallographic data (CIF files) of all the synthesized compounds, spectral data of all compounds, and copies of 1H, 13C NMR and MS spectra of products associated with this article.
- Supporting Information
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