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N-heterocyclic carbene adducts of cyclopalladated ferrocenylpyridine containing chloride or iodide anions: synthesis, crystal structures and application in the coupling of terminal alkynes with arylboronic acids

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Abstract

Two air-stable N-heterocyclic carbene (NHC) adducts of cyclopalladated ferrocenylpyridine containing chloride or iodide anions 2–3 have been easily prepared from the bridge-splitting reaction of the palladacyclic dimer 1 and anion exchange reaction, respectively. They were characterized by elemental analysis, IR, 1H, and 13C NMR. Additionally, the structures of these complexes were determined by single-crystal X-ray analysis. These adducts have been successfully applied to the coupling of terminal alkynes with arylboronic acids under atmospheric conditions.

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References

  1. Tsuji J (2004) Palladium reagents and catalysts. Wiley, Chichester

    Book  Google Scholar 

  2. Chinchilla R, Nájera C (2007) Chem Rev 107:874

    Article  CAS  Google Scholar 

  3. Chinchilla R, Nájera C (2011) Chem Soc Rev 40:5084

    Article  CAS  Google Scholar 

  4. Doucet H, Hierso JC (2007) Angew Chem Int Ed 46:834

    Article  CAS  Google Scholar 

  5. Consorti CS, Flores FR, Rominger F, Dupont J (2006) Adv Synth Catal 348:133

    Article  CAS  Google Scholar 

  6. Zou G, Zhu JR, Tang J (2003) Tetrahedron Lett 44:8709

    Article  CAS  Google Scholar 

  7. Pan CD, Luo F, Wang WH, Ye ZS, Cheng J (2009) Tetrahedron Lett 50:5044

    Article  CAS  Google Scholar 

  8. Rao HH, Fu H, Jiang YY, Zhao YF (2010) Adv Synth Catal 352:458

    Article  CAS  Google Scholar 

  9. Zhou MB, Wei WT, Xie YX, Lei Y, Li JH (2010) J Org Chem 75:5635

    Article  CAS  Google Scholar 

  10. Yang F, Wu YJ (2007) Eur J Org Chem 3476

  11. Nie XP, Liu SL, Zong Y, Sun PP, Bao JC (2011) J Organomet Chem 696:1570

    Article  CAS  Google Scholar 

  12. Enders D, Niemeier O, Henseler A (2007) Chem Rev 107:5606

    Article  CAS  Google Scholar 

  13. Hahn FE, Jahnke MC (2008) Angew Chem Int Ed 47:3122

    Article  CAS  Google Scholar 

  14. Fortman GC, Nolan SP (2011) Chem Soc Rev 40:5151

    Article  CAS  Google Scholar 

  15. Bedford RB (2003) Chem Commun 1787

  16. Dupont J, Pfeffer M (2008) Palladacycles. Wiley-VCH, Weinheim

    Book  Google Scholar 

  17. Xu C, Wang ZQ, Fu WJ, Lou XH, Li YF, Cen FF, Ma HJ, Ji BM (2009) Organometallics 28:1909

    Article  CAS  Google Scholar 

  18. Xu C, Zhang YP, Wang ZQ, Fu WJ, Hao XQ, Xu Y, Ji BM (2010) Chem Commun 6852

  19. Xu C, Wang ZQ, Li Z, Wang WZ, Hao XQ, Fu WJ, Gong JF, Ji BM, Song MP (2012) Organometallics 31:798

    Article  CAS  Google Scholar 

  20. Xu C, Lou XH, Wang ZQ, Fu WJ (2012) Transition Met Chem 37:519

    Article  CAS  Google Scholar 

  21. Delaude L, Szypa M, Demonceau A, Noels AF (2002) Adv Synth Catal 344:749

    Article  CAS  Google Scholar 

  22. Xu C, Wang ZQ, Zhang YP, Dong XM, Hao XQ, Fu WJ, Ji BM, Song MP (2011) Eur J Inorg Chem 4878

  23. Cheng J, Sun YH, Wang F, Guo MJ, Xu JH, Pan Y, Zhang ZG (2004) J Org Chem 69:5428

    Article  CAS  Google Scholar 

  24. Liang B, Dai MJ, Chen JH, Yang Z (2005) J Org Chem 70:391

    Article  CAS  Google Scholar 

  25. Yang F, Cui XL, Li YN, Zhang JL, Ren GR, Wu YJ (2007) Tetrahedron 63:1963

    Article  CAS  Google Scholar 

  26. Ngassa FN, Lindsey EA, Haines BE (2009) Tetrahedron 65:4085

    Article  CAS  Google Scholar 

  27. Sheldrick GM (2008) Acta Crystallogr A 64:112

    Article  Google Scholar 

  28. Pedireddi VR, Reddy DS, Goud BS, Craig DC, Rae AD, Desiraju GR (1994) J Chem Soc Perkin Trans 2:2353

    Google Scholar 

  29. Herrmann WA, Böhm VPW, Reisinger CP (1999) J Organomet Chem 576:23

    Article  CAS  Google Scholar 

  30. Bedford RB, Cazin CSJ (2003) Organometallics 22:987

    Article  CAS  Google Scholar 

  31. Harmata M (2010) Silver in organic chemistry. Wiley, Weinheim

    Book  Google Scholar 

Download references

Acknowledgments

We are grateful to the National Natural Science Foundation of China (No. 21272110 and 20902043) for financial support of this work.

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang, 471022, Henan, China

    Hong-Mei Li, Chen Xu, Xin-Hua Lou & Zhi-Qiang Wang

  2. Department of Chemistry, Zhengzhou University, Zhengzhou, 450052, Henan, China

    Lu-Meng Duan, Zhen Li & Yao-Ting Fan

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  1. Hong-Mei Li
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  2. Chen Xu
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  3. Lu-Meng Duan
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  4. Xin-Hua Lou
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  5. Zhi-Qiang Wang
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  6. Zhen Li
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  7. Yao-Ting Fan
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Correspondence to Chen Xu.

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Li, HM., Xu, C., Duan, LM. et al. N-heterocyclic carbene adducts of cyclopalladated ferrocenylpyridine containing chloride or iodide anions: synthesis, crystal structures and application in the coupling of terminal alkynes with arylboronic acids. Transition Met Chem 38, 313–318 (2013). https://doi.org/10.1007/s11243-013-9695-7

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  • DOI: https://doi.org/10.1007/s11243-013-9695-7

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