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Oxidation of electron deficient olefins using a copper(II) complex based on a bis-benzimidazole diamide ligand

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Abstract

New bis-benzimidazole based diamide ligands N, N′-bis(2-methyl benzimidazolyl)-benzene-1,3-dicarboxamide [GBBA] and N-Octyl-N, N′-bis(2-methyl benzimidazolyl)-benzene- 1,3-dicarboxamide [O-GBBA] have been synthesized and utilized to prepare Cu(II) complexes of general composition [Cu(GBBA)X 2] · nH2O and [Cu(O-GBBA)X2] · n H2O, where X is an exogenous anionic ligand (X =  Cl−, NO −3 , SCN−). The oxidation of electron deficient olefins has been investigated using [Cu(O-GBBA)X2] · nH2O as catalyst and TBHP as an alternate source of oxygen. The respective ketonic products have been isolated and characterized by 1H-NMR. The complex [Cu(GBBA)(NO3)2] · 4H2O has been characterized structurally. It crystallizes in a monoclinic space group C2/c. Low temperature EPR spectra have been obtained for the complexes that shows gII >  gI >  2.0024, indicating a tetragonal geometry in the solution state. The complexes display a quasi reversible redox wave due to the Cu(II)/Cu(I) reduction process. The E1/2 values shift anodically as NO −3  <  SCN−  < Cl−.

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Acknowledgements

We greatly acknowledge financial support from the Department of Science and Technology, India, for project no.SR /S1 /IC-35 /2003.

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Authors and Affiliations

  1. Department of Chemistry, University of Delhi, Delhi, 110007, India

    Manisha Singla & Pavan Mathur

  2. Acharya Narendra Dev College, University of Delhi, Delhi, 110007, India

    Manisha Gupta

  3. Guru Nanak Dev University, Amritsar, India

    M. S. Hundal

Authors
  1. Manisha Singla
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  2. Pavan Mathur
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  3. Manisha Gupta
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  4. M. S. Hundal
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Corresponding author

Correspondence to Pavan Mathur.

Appendix A: supporting information

Appendix A: supporting information

Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre,CCDC 638406. Copies of this information can be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (Fax: 44-1223-336-033; E-mail:deposit@ccdc.cam.ac.uk or www: http://www.ccdc.cam.ac.uk/data_request.cif).

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Singla, M., Mathur, P., Gupta, M. et al. Oxidation of electron deficient olefins using a copper(II) complex based on a bis-benzimidazole diamide ligand. Transition Met Chem 33, 175–182 (2008). https://doi.org/10.1007/s11243-007-9029-8

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