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Mechanistic insight into the preactivation of a modern palladium catalyst precursor in phosphine-free Heck reactions

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Abstract

The use of well-defined trans-dichlorobis(diethanolamine-N)palladium(II) complex (trans-[PdCl2(DEA)2]) as a new, modern, and effective Heck precatalyst is reported. The mechanism of the key, initial steps of the reaction, i.e., the formation of the Pd(0) complex, is examined using density functional theory.

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References

  1. De Vries JG (2001) Can J Chem 79:1086

    Article  Google Scholar 

  2. Heck R (1979) Acc Chem Res 12:146

    Article  CAS  Google Scholar 

  3. Alonso DA, Nájera C, Pácheco MC (2000) Org Lett 2:1823

    Article  CAS  Google Scholar 

  4. Consorti CS, Zanini ML, Leal S, Ebeling G, Dupont J (2003) Org Lett 5:983

    Article  CAS  Google Scholar 

  5. Wang R, Twamley B, Shreeve JM (2006) J Org Chem 71:426

    Article  CAS  Google Scholar 

  6. Jin CM, Twamley B, Shreeve JM (2005) Organometallics 24:3020

    Article  CAS  Google Scholar 

  7. Cui X, Li J, Zhang ZP, Fu Y, Liu L, Guo QX (2007) J Org Chem 72:9342

    Article  CAS  Google Scholar 

  8. Amatore C, Jutand A (2000) Acc Chem Res 33:314

    Article  CAS  Google Scholar 

  9. Cabri W, Candiani I (1995) Acc Chem Res 28:2

    Article  CAS  Google Scholar 

  10. Emmerson DPG, Hems WP, Davis BG (2006) Org Lett 8:207

    Article  CAS  Google Scholar 

  11. Lu G, Li X, Zhou Z, Chan WL, Chan ASC (2001) Tetrahedron Asymm 12:2147

  12. Wu X, Li X, McConville M, Saidi O, Xiao J (2006) J Mol Catal A 247:153

    Article  CAS  Google Scholar 

  13. Patti A, Pedotti S (2003) Tetrahedron Asymm 14:597

  14. Petrović ZD, Djuran MI, Heinemann FW, Rajković S, Trifunović S (2006) Bioorg Chem 34:225

    Article  Google Scholar 

  15. Cui X, Li Z, Tao CZ, Xu Y, Li J, Liu L, Guo QX (2006) Org Lett 8:2467

    Article  CAS  Google Scholar 

  16. Cui X, Qin T, Wang JR, Liu L, Guo QX (2007) Synthesis 3:393

    Google Scholar 

  17. Hong JL, Wang L (2006) Eur J Org Chem 22:5099

    Google Scholar 

  18. Jensen DR, Schultz MJ, Mueller JA, Sigman MS (2003) Angew Chem Int Ed 42:3810

    Article  CAS  Google Scholar 

  19. Marti J (2001) Chem Phys 265:263

    Article  CAS  Google Scholar 

  20. Gaussian Inc. (2003) Gaussian 03, revision E.01-SMP. Gaussian Inc., Pittsburgh, PA

  21. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785

    Article  CAS  Google Scholar 

  22. Becke AD (1993) J Chem Phys 98:5648

    Article  CAS  Google Scholar 

  23. Hay PJ, Wadt WR (1985) J Chem Phys 82:270

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work is supported by the Ministry of Science and the Environment of Serbia, project No. 142013 B.

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Authors and Affiliations

  1. Faculty of Science, University of Kragujevac, 34000, Kragujevac, Serbia

    Zorica D. Petrović, Svetlana Marković, Dušica Simijonović & Vladimir Petrović

Authors
  1. Zorica D. Petrović
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  2. Svetlana Marković
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  3. Dušica Simijonović
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  4. Vladimir Petrović
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Corresponding author

Correspondence to Svetlana Marković.

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Petrović, Z.D., Marković, S., Simijonović, D. et al. Mechanistic insight into the preactivation of a modern palladium catalyst precursor in phosphine-free Heck reactions. Monatsh Chem 140, 371–374 (2009). https://doi.org/10.1007/s00706-008-0035-0

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  • DOI: https://doi.org/10.1007/s00706-008-0035-0

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