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New (NHC)Pd(II)(PPh3) complexes: synthesis, characterization, crystal structure and its application on Sonogashira and Mizoroki–Heck cross-coupling reactions

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Abstract

In this study, new six Pd-based complexes containing mixture N-heterocyclic carbene (NHC) and triphenylphosphine (PPh3) ligands were synthesized from the reaction of the (NHC)PdI2(pyridine) with PPh3. The new (NHC)PdI2(PPh3) complexes were characterized using FTIR, 1H-NMR, 13C-NMR, and 31P-NMR spectroscopy and elemental analyses techniques. These spectra are consistent with the proposed formula. Molecular and crystal structure of two complexes was obtained using single-crystal X-ray diffraction method. Based on the crystal results, a cis geometry was assigned to all the complexes. These new complexes have been examined as the catalyst in the Sonogashira cross-coupling reaction. The catalytic conversions of the complexes were obtained between 71 and 99% from the reaction of phenylacetylene and aryl bromides. Also, these new complexes have been examined as the catalyst in the Mizoroki–Heck cross-coupling reaction. The catalytic conversions of the complexes were obtained between 80 and 100% from the reaction of styrene and aryl bromides.

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Acknowledgements

The authors acknowledge Dokuz Eylul University for the use of the Rigaku Oxford Xcalibur Eos Diffractometer (purchased under University Research Grant no.: 2010.KB.FEN.13). The authors thank the Inonu University Faculty of Science Department of Chemistry for the spectroscopy and elemental analysis characterization of compounds.

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Correspondence to Aydın Aktaş.

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Appendix A: Supplementary data

Appendix A: Supplementary data

CCDC 1897240 for 1b and 1897153 for 1f contain the supplementary crystallographic data. Copies of the data can be obtained free of charge at http://www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Center, 12, Union Road, Cambridge CB2 1EZ, UK. fax: (+44) 1223-336-033, e-mail: deposit@ccdc.cam.ac.uk.

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Erdemir, F., Aktaş, A., Barut Celepci, D. et al. New (NHC)Pd(II)(PPh3) complexes: synthesis, characterization, crystal structure and its application on Sonogashira and Mizoroki–Heck cross-coupling reactions. Chem. Pap. 74, 99–112 (2020). https://doi.org/10.1007/s11696-019-00859-x

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  • DOI: https://doi.org/10.1007/s11696-019-00859-x

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