Formation of Imidazolidine-benzothiazole–Copper(II) Complexes via a Copper-Mediated Room-Temperature C–H Activation of Imidazolidinecarbothioamides

Abstract

imidazolidine-1-carbothioamide, and unsymmetrical thiourea, with copper(II) chloride or bromide results in aryl sp 2 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 Hdonor 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.