Synthesis 2014; 46(14): 1886-1900
DOI: 10.1055/s-0033-1339127
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Santosh K. Sahoo
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781 039, Assam, India   Fax: +91(361)26909762   Email: patel@iitg.ernet.in
,
Himanshu Sekhar Jena
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781 039, Assam, India   Fax: +91(361)26909762   Email: patel@iitg.ernet.in
,
Ganesh Majji
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781 039, Assam, India   Fax: +91(361)26909762   Email: patel@iitg.ernet.in
,
Bhisma K. Patel*
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781 039, Assam, India   Fax: +91(361)26909762   Email: patel@iitg.ernet.in
› Author Affiliations
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.

Supporting Information

 
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