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Synthesis and Crystal Structure of a Chelating N-Heterocyclic Carbene Palladium Complex Containing N-(3-Bromopropyl)-N’-thioether di-functionalized Imidazol-2-ylidene

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Abstract

A chelating N-heterocyclic carbene palladium complex (3) containing N-(3-bromopropyl)-N’-thioether di-functionalized imidazol-2-ylidene was synthesized by the direct metalation of N-(3-bromopropyl)-N’-thioether di-functionalized imidazolium bromide (2) with Pd(OAc)2 in the presence of NaOAc and NaBr at room temperature using CH2Cl2 as solvent. The structure was characterized by NMR, HR-MS and X-ray crystallography. The results showed that complex 3 consists of two independent molecules with configuration of SC, RS in molecule a, and SC, SS in molecule b, respectively. The crystal is triclinic, P1 space group, with a = 8.4815(3), b = 8.6338(3), c = 19.2371(7) Å, V = 1245.66(8) Å3, and Z = 2 (at 293(2)K).

Graphical Abstract

A chelating N-heterocyclic carbene palladium complex (3) consists of two independent molecules with configurations of SC, RS and SC, SS respectively has been synthesized through the direct metalation of the precursor imidazolium bromide (2).

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Scheme 1
Fig. 1

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Data Availability

CCDC 2312021 contains supplementary crystallographic data for complex 3. These data may be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data_request/cif or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+ 44) 1223–336-033; or e-mail: deposit@ccdc.cam.ac.uk. Atomic coordinates for the optimized structure are available from L. Yang upon request.

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Acknowledgements

This work was supported by the Natural Science Foundation of Henan Province (No. 242300420186) and the Innovative Funds Plan of Henan University of Technology (No. 2020ZKCJ29).

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Authors and Affiliations

  1. School of Chemistry & Chemical Engineering, Henan University of Technology, Zhengzhou, 450001, People’s Republic of China

    Yongmei Xiao, Yaowen Liu, Liangru Yang, Yingjun Wang, Jinwei Yuan & Lingbo Qu

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  1. Yongmei Xiao
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  2. Yaowen Liu
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  3. Liangru Yang
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  4. Yingjun Wang
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  5. Jinwei Yuan
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Contributions

Y. Xiao, Y. Liu, and Y. Wang carried out synthesis and characterization. L. Yang, J. Yuan, and L. Qu carried out data analysis, partly wrote the main manuscript and acquire fund. All authors reviewed the manuscript.

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Correspondence to Liangru Yang or Jinwei Yuan.

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Xiao, Y., Liu, Y., Yang, L. et al. Synthesis and Crystal Structure of a Chelating N-Heterocyclic Carbene Palladium Complex Containing N-(3-Bromopropyl)-N’-thioether di-functionalized Imidazol-2-ylidene. J Chem Crystallogr (2024). https://doi.org/10.1007/s10870-024-01012-7

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