Transition Metal Chemistry

, Volume 43, Issue 4, pp 347–353 | Cite as

Dinuclear NHC–palladium(II) complexes: synthesis,characterization and application to Suzuki–Miyaura cross-coupling reactions

Article
  • 49 Downloads

Abstract

Four dinuclear N-heterocyclic carbene–palladium(II) complexes 14 were prepared and characterized by elemental analysis and spectroscopic methods. The X-ray crystal structure of complex 2 showed a dinuclear framework in which N-heterocyclic ligands bridge between two square planar palladium(II) units. Each palladium center is surrounded by an imidazolylidene, a nitrogen atom from the central linking ligand, and two trans-chloride ligands. These dinuclear NHC–palladium(II) complexes exhibited efficient catalytic activities for the Suzuki–Miyaura coupling of aryl and benzyl chlorides with arylboronic acids.

Graphical Abstract

Notes

Acknowledgements

We are grateful to the National Natural Sciences Foundation of China (nos. U1404205, 21572126 and 21202095), the Program for Science & Technology Innovation Talents in Universities of Henan Province (14HASTIT016), Innovation Scientists and Technicians Troop Construction Projects of Henan Province, and Key Scientific and Technological Project of Henan Province (152102410056) for financial support.

Supplementary material

11243_2018_224_MOESM1_ESM.doc (3.9 mb)
Supplementary material 1 (DOC 3998 kb)

References

  1. 1.
    Liu C, Liu G, Zhao H (1048) Chin J Chem 2016:34Google Scholar
  2. 2.
    Zhang G, Zhang W, Luan Y, Han X, Ding C (2015) Chin J Chem 33:705CrossRefGoogle Scholar
  3. 3.
    Valente C, Calimsiz S, Hoi K-H, Mallik D, Sayah M, Organ MG (2012) Angew Chem Int Ed 51:3314CrossRefGoogle Scholar
  4. 4.
    Jiang L, Li Z, Zhao D (2010) Chin. J. Org. Chem. 30:200Google Scholar
  5. 5.
    Molander GA, Canturk B (2009) Angew Chem Int Ed 48:9240CrossRefGoogle Scholar
  6. 6.
    Fu GC (2008) Acc Chem Res 41:1555CrossRefGoogle Scholar
  7. 7.
    Alonso F, Beletskaya IP, Yus M (2008) Tetrahedron 64:3047CrossRefGoogle Scholar
  8. 8.
    Marion N, Nolan SP (2008) Acc Chem Res 41:1440CrossRefGoogle Scholar
  9. 9.
    Corbet J-P, Mignani G (2006) Chem Rev 106:2651CrossRefGoogle Scholar
  10. 10.
    Suzuki A (1999) J Organomet Chem 576:147CrossRefGoogle Scholar
  11. 11.
    Miyaura N, Suzuki A (1995) Chem Rev 95:2457CrossRefGoogle Scholar
  12. 12.
    Menon RS, Biju AT, Nair V (2015) Chem Soc Rev 44:5040CrossRefGoogle Scholar
  13. 13.
    Tang Y, Yang F, Nie S, Wang L, Luo Z, Lu H (2015) Chin J Org Chem 35:705CrossRefGoogle Scholar
  14. 14.
    Budagumpi S, Haque RA, Salman AW (2012) Coord Chem Rev 256:1787CrossRefGoogle Scholar
  15. 15.
    Yuan D, Huynh HV (2012) Molecules 17:2491CrossRefGoogle Scholar
  16. 16.
    Fortman GC, Nolan SP (2011) Chem Soc Rev 40:5151CrossRefGoogle Scholar
  17. 17.
    Droge T, Glorius F (2010) Angew Chem Int Ed 49:6940CrossRefGoogle Scholar
  18. 18.
    Diez-Gonzalez S, Marion N, Nolan Steven P (2009) Chem Rev 109:3612CrossRefGoogle Scholar
  19. 19.
    Nair V, Vellalath S, Babu BP (2008) Chem Soc Rev 37:2691CrossRefGoogle Scholar
  20. 20.
    Hahn FE, Jahnke MC (2008) Angew Chem Int Ed 47:3122CrossRefGoogle Scholar
  21. 21.
    Dunsford JJ, Cavell KJ (2014) Organometallics 33:2902CrossRefGoogle Scholar
  22. 22.
    Rajabi F, Thiel WR (1873) Adv Synth Catal 2014:356Google Scholar
  23. 23.
    Teci M, Brenner E, Matt D, Toupet L (2013) Eur J Inorg Chem 16:2841CrossRefGoogle Scholar
  24. 24.
    Tu T, Sun Z, Fang W, Xu M, Zhou Y (2012) Org Lett 14:4250CrossRefGoogle Scholar
  25. 25.
    Zhang Y, Yin S-C, Lu J-M (2015) Tetrahedron 71:544CrossRefGoogle Scholar
  26. 26.
    Gu Z-S, Chen W-X, Shao L-X (2014) J Org Chem 79:5806CrossRefGoogle Scholar
  27. 27.
    Shen X-B, Zhang Y, Chen W-X, Xiao Z-K, Hu T-T, Shao L-X (1984) Org Lett 2014:16Google Scholar
  28. 28.
    Xiao Z-K, Yin H-Y, Lu J-M (2014) Inorg Chim Acta 423:106CrossRefGoogle Scholar
  29. 29.
    Micksch M, Tenne M, Strassner T (2014) Organometallics 33:3966CrossRefGoogle Scholar
  30. 30.
    Shen A, Ni C, Cao Y-C, Zhou H, Song G-H, Ye X-F (2014) Tetrahedron Lett 55:3278CrossRefGoogle Scholar
  31. 31.
    Yuan D, Zhang Q, Liao S, Xiong W, Yuan L, Cai Q, Yang M, Li X, Jiang Y, Liu Y, Li P, Xu Z, Sun P, Geng H (2015) Chin J Org Chem 35:961CrossRefGoogle Scholar
  32. 32.
    Yang J, Li P, Zhang Y, Wang L (2014) J Organomet Chem 766:73CrossRefGoogle Scholar
  33. 33.
    Yang J, Li P, Zhang Y, Wang L (2014) Dalton Trans 43:7166CrossRefGoogle Scholar
  34. 34.
    Yang J, Wang L (2012) Dalton Trans 41:12031CrossRefGoogle Scholar
  35. 35.
    Han Y, Huynh HV, Tan GK (2007) Organometallics 26:6447CrossRefGoogle Scholar
  36. 36.
    Wang T, Liu L, Xu K, Xie H, Shen H, Zhao W-X (2016) RSC Adv 6:100690CrossRefGoogle Scholar
  37. 37.
    Wang T, Xu K, Meng T, Zhang A, Wang H, Shen S, Liu L (2017) Chin J Org Chem 37:1794CrossRefGoogle Scholar
  38. 38.
    Wang T, Xie H, Liu L, Zhao W-X (2016) J Organomet Chem 804:73CrossRefGoogle Scholar
  39. 39.
    Wang T, Xu K, Liu L, Xie H, Li Y, Zhao W-X (2016) Transit Met Chem 41:525CrossRefGoogle Scholar
  40. 40.
    Barnes JC, Jurícek M, Strutt NL, Frasconi M, Sampath S, Giesener MA, McGrier PL, Bruns CJ, Stern CL, Sarjeant AA, Stoddart JF (2013) J Am Chem Soc 135:183CrossRefGoogle Scholar
  41. 41.
    Sheldrick GM (1997) SHELXS-97, program for crystal structure solution. University of Göttingen, GöttingenGoogle Scholar
  42. 42.
    Sheldrick GM (1997) SHELXL-97, program for crystal structure refinement. University of Göttingen, GöttingenGoogle Scholar
  43. 43.
    Ouyang K, Xi Z (2013) Acta Chim Sin 71:13CrossRefGoogle Scholar

Copyright information

© Springer International Publishing AG, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Henan Engineering Laboratory of Green Synthesis for Pharmaceuticals, School of Chemistry and Chemical EngineeringShangqiu Normal UniversityShangqiuPeople’s Republic of China
  2. 2.Henan Key Laboratory of Biomolecular Recognition and Sensing, School of Chemistry and Chemical EngineeringShangqiu Normal UniversityShangqiuPeople’s Republic of China

Personalised recommendations