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Mono- and dinuclear palladium(II) complexes incorporating 1,2,3-triazole-derived mesoionic carbenes: syntheses, solid-state structures and catalytic applications

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Abstract

Two 1,2,3-triazole-derived monocationic salts 3 and 4 bearing N-aryl wingtips were prepared using copper-catalyzed “click” reactions followed by alkylations with iodomethane. Employing a silver–carbene transfer method, two dinuclear palladium(II) complexes of triazolin-5-ylidenes (5/6) were obtained, the former of which has been reported previously. Bridge-cleavage reaction of 5 as a representative with PPh3 yielded cis-configured mesoionic carbene/phosphine hybrid complex cis-7 and homoleptic bis(phosphine) complex 8, suggesting the presence of a ligand exchange process. In contrast, bridge breakages of 5/6 with pyridine cleanly afforded PEPPSI-type complexes 9 and 10 in near quantitative yields. Finally, all complexes were exploited to catalyze Mizoroki–Heck coupling reactions with aryl bromides as the substrates, and PEPPSI-type complex 9 was found to be the best performer generally giving good to excellent yields.

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Fig. 1
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Notes

  1. For selected reviews, see [1,2,3,4,5,6,7,8,9,10].

  2. For selected examples of the type I with imdazolin-2-ylidenes as the supporting ligands, see [11,12,13]. For selected examples of the type I with benzimdazolin-2-ylidenes as the supporting ligands, see [14, 15].

  3. For selected reviews on PEPPSI-type complexes, see [16, 17].

  4. See [18].

  5. For selected reviews on mesoionic carbenes, see [19,20,21,22,23,24].

  6. See [25,26,27].

  7. See [28].

  8. For the paper providing the first example of 1,2,3-triazolin-5-ylidene complex, see [29]. For selected reviews on 1,2,3-triazolin-5-ylidenes and their complexes, see [30, 31].

  9. For selected reviews on copper-catalyzed click reactions, see [32,33,34].

  10. For selected examples of hybrid complexes bearing MICs in analogy to I, see [35,36,37,38,39].

  11. Complex [CuCl(IPr)] has been previously employed to catalyze azide-alkyne cycloaddition reactions. For selected papers and reviews, see [40,41,42].

  12. For earlier reports on the syntheses and characterizations of triazole 1 and salt 3, see [43,44,45].

  13. The aryl C–Ha proton expectedly give a doublet with a small coupling constant of ~ 2–3 Hz, due to (i) the absence of protons attached to the Cortho atoms and (ii) the splitting by C–H protons of the Cmeta atoms. In our case, a singlet was observed probably due to the low resolution of NMR spectrometer.

  14. For a review on agostic and anagostic interactions, see [46].

  15. For selected publications reporting the crystal data of trans-[PdI2(PPh3)2], see [47, 48].

  16. The term “transphobia effect” was first coined by Vicente and Jones’s groups. For this paper, see [49].

  17. For selected examples, see [50, 51].

  18. For a paper on the definition of π–π stacking, see [52].

  19. See [53].

  20. See [54].

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Acknowledgements

This work is financially supported by Capacity Building for Sci-Tech Innovation-Fundamental Scientific Research Funds (Grant No. 025185305000/208) and Department of Education of Guangdong Province (Grant No. 2016KCXTD005, 2017KQNCX204).

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Author notes

  1. **n Zhang and Xuechao Yan are contributed equally to this work.

Authors and Affiliations

  1. Department of Chemistry, Capital Normal University, Bei**g, 100048, People’s Republic of China

    **n Zhang, Xuechao Yan, Bo Zhang, Ran Wang & Shuai Guo

  2. School of Chemical and Environmental Engineering, Wuyi University, Jiangmen, 529020, Guangdong Province, People’s Republic of China

    Shiyong Peng

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  1. **n Zhang
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Correspondence to Shuai Guo.

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Zhang, X., Yan, X., Zhang, B. et al. Mono- and dinuclear palladium(II) complexes incorporating 1,2,3-triazole-derived mesoionic carbenes: syntheses, solid-state structures and catalytic applications. Transit Met Chem 44, 39–48 (2019). https://doi.org/10.1007/s11243-018-0267-8

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