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Nickel(II) complexes containing ONS donor ligands: Synthesis, characterization, crystal structure and catalytic application towards C-C cross-coupling reactions

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Abstract

Nickel(II) complexes containing thiosemicarbazone ligands [Ni(L)2] (1-3) (L = 9,10-phenanthrenequinonethiosemicarbazone (HL1), 9,10-phenanthrenequinone-N-methylthio semicarbazone (HL2) and 9, 10-phenanthrenequinone-N-phenylthiosemicarbazone (HL3)) have been synthesized and characterized by elemental analysis and spectroscopic (IR, UV-Vis, 1H, 13C-NMR and ESI mass) methods. The molecular structures of complexes 1 and 2 were identified by means of single-crystal X-ray diffraction analysis. The analysis revealed that the complexes possess a distorted octahedral geometry with the ligand coordinating in a uni-negative tridentate ONS fashion. The catalytic activity of complexes towards some C–C coupling reactions (viz., Kumada-Corriu, Suzuki-Miyaura and Sonogashira) has been examined. The complexes behave as efficient catalysts in the Kumada-Corriu and Sonogashira coupling reactions rather than Suzuki-Miyaura coupling.

Nickel(II) complexes bearing 9,10-phenanthrenequinone N-substituted thiosemicarbazone ligands were synthesized and characterized. The X-ray crystal structure of the complexes revealed a distorted octahedral geometry around the metal centre. These nickel complexes exhibited better catalytic activity in Kumada-Corriu and Sonogashira cross-coupling reactions than in Suzuki-Miyaura reaction.

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Acknowledgements

The authors express their sincere thanks to Council of Scientific and Industrial Research (CSIR), New Delhi, India [Grant No. 01(2437)/10/EMR-II] for financial support. One of the authors (PA) thanks CSIR for the award of Senior Research Fellowship. The authors wish to record grateful thanks to Dr. Matthias Zeller, Department of Chemistry, Youngstown State University, Youngstown, USA for crystal data collections.

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Authors and Affiliations

  1. Department of Chemistry, Periyar University, Salem, 636011, Tamil Nadu, India

    PANNEERSELVAM ANITHA, RAJENDRAN MANIKANDAN, PARANTHAMAN VIJAYAN, GOVINDAN PRAKASH & PERIASAMY VISWANATHAMURTHI

  2. Department of Chemistry, Howard University, 525 College Street NW, Washington, DC, 20059, USA

    RAY JAY BUTCHER

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  1. PANNEERSELVAM ANITHA
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  2. RAJENDRAN MANIKANDAN
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Correspondence to PERIASAMY VISWANATHAMURTHI.

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Supplementary Information

CCDC 999389, 979255 contain the supplementary crystallographic data for the complexes 1 and 2. These data can be obtained free of charge via www.ccdc.cam.ac.uk/datarequest/cif. The NMR (1H and 13C), ESI-Mass spectra of complexes and optimized reaction conditions for Kumada-Corriu coupling and Sonogashira coupling are given as supplementary materials (figures S1–S14) and are available at www.ias.ac.in/chemsci.

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ANITHA, P., MANIKANDAN, R., VIJAYAN, P. et al. Nickel(II) complexes containing ONS donor ligands: Synthesis, characterization, crystal structure and catalytic application towards C-C cross-coupling reactions. J Chem Sci 127, 597–608 (2015). https://doi.org/10.1007/s12039-015-0811-4

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