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N, N′-Olefin functionalized Bis-Imidazolium Pd(II) chloride N-Heterocyclic carbene complex builds a supramolecular framework and shows catalytic efficacy for ‘C–C’ coupling reactions

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Abstract

The ligand 3,3′-(p-phenylenedimethylene)bis{1-(2-methylallyl)} imidazolium bromide (1) and its Palladium(II) N-heterocyclic carbene (NHC) complex (3) has been synthesized and characterized by several spectroscopic techniques and the solid-state structure of 3 has been determined by single crystal X-ray diffraction studies. The Pd(II) complex possesses ring head to tail π– π stacking interactions (3.767 A ∘) through imidazole rings. Complex 3 catalyzes Suzuki-Miyaura ‘C–C’ coupling reaction. DFT calculations have been used to understand the HOMO/LUMO energy and hence the stability and reactivity of Pd(II) complex in syn and anti-configuration.

Palladium(II) N-heterocyclic carbene (NHC) complex (3) of the ligand 3,3'-(pphenylenedimethylene) bis{1-(2-methylallyl)}imidazolium bromide has been synthesized and characterized by several spectroscopic techniques and finally the solid-state structure of 3 has been determined by single-crystal X-ray diffraction studies. The Pd(II) complex possesses ring head to tail Π–Π stacking interaction (3.767 Ǻ) through imidazole rings. Complex 3 catalyzes Suzuki–Miyaura ‘C–C’ coupling reaction. DFT calculations were performed to know HOMO/LUMO energy and hence the stability and reactivity of Pd(II) complex in syn- and anti-configuration.

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Acknowledgements

GR and TS have made a substantial contribution to experimental design, to acquisition of data, analysis, and manuscript preparation. SKS performed the crystallographic study. GR performed the DFT study. AM, SKC and JD analyzed the data and revised the final manuscript. All authors read and approved the final manuscript. Authors would like to extend their appreciation to Dr. Biswajit Maji, Assistant Professor, Dept. of Chemistry, Indira Gandhi National Tribal University, Amarkantak, India, for helping in catalysis data collection and Prof. (Dr.) Chitta Ranjan Sinha, Dept. of Chemistry, Jadavpur University, Kolkata, India, for his valuable suggestions.

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Authors and Affiliations

  1. Department of Basic Science and Humanities, Global Institute of Science and Technology, Haldia, 721657, India

    GOURISANKAR ROYMAHAPATRA

  2. Department of Chemistry, Jadavpur University, Kolkata, 700 032, India

    GOURISANKAR ROYMAHAPATRA & AMBIKESH MAHAPATRA

  3. School of Applied Sciences, Haldia Institute of Technology, Haldia, 721 657, India

    GOURISANKAR ROYMAHAPATRA, TAPASTARU SAMANTA & JOYDEV DINDA

  4. Department of Physics, Mugberia Gangadhar Mahavidyalaya, Purba Medinipur, 721 425, India

    SAIKAT KUMAR SETH

  5. Department of Chemistry, Indian Institute of Engineering Science and Technology, Howrah, 711 103, India

    TAPASTARU SAMANTA & SHYAMAL KUMAR CHATTOPADHYAY

  6. Department of Chemistry, ITM University, Turari Campus, Gwalior, 474 001, India

    JOYDEV DINDA

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  1. GOURISANKAR ROYMAHAPATRA
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Tables S1 and S2 and figure S1 are available at www.ias.ac.in/chemsci.

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ROYMAHAPATRA, G., SAMANTA, T., SETH, S.K. et al. N, N′-Olefin functionalized Bis-Imidazolium Pd(II) chloride N-Heterocyclic carbene complex builds a supramolecular framework and shows catalytic efficacy for ‘C–C’ coupling reactions. J Chem Sci 127, 1057–1065 (2015). https://doi.org/10.1007/s12039-015-0870-6

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