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Palladium supported on triphenylphosphine-functionalized porous organic polymer: an efficient heterogeneous catalyst for aminocarbonylation

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Abstract

An efficient route for the catalytic synthesis of aryl amides via the aminocarbonylation of aryl iodides with amines is described using palladium supported on triphenylphosphine-functionalized porous organic polymer (Pd@KAPs(Ph-PPh3)) as the catalyst. Under low carbon monoxide pressure, the catalyst exhibited remarkable activity, and only 0.5 mol% palladium loading was required to achieve moderate to excellent yields (70–97 %) of aryl amides. The catalyst can be easily separated by a simple filtration process and recycled up to seven times with only minor loss of activity. The salient features of this protocol are the simplicity in handling of catalyst, low CO pressure, good functional group tolerance, high catalytic activity, negligible palladium leaching and effective catalyst recyclability.

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References

  1. Pattabiraman VR, Bode JW (2011) Nature 480:471

    Article  CAS  Google Scholar 

  2. Zhang DW, Zhao X, Hou JL, Li ZT (2012) Chem Rev 112:5271

    Article  CAS  Google Scholar 

  3. Gadge ST, Bhanage BM (2014) RSC Adv 4:10367

    Article  CAS  Google Scholar 

  4. Sumino S, Fusano A, Fukuyama T, Ryu I (2014) Acc Chem Res 47:1563

    Article  CAS  Google Scholar 

  5. Wu X-F, Neumann H, Beller M (2013) Chem Rev 113:1

    Article  Google Scholar 

  6. Omae I (2011) Coord Chem Rev 255:139

    Article  CAS  Google Scholar 

  7. Wu X-F, Neumann H, Beller M (2011) Chem Soc Rev 40:4986

    Article  CAS  Google Scholar 

  8. Xu T, Alper H (2014) J Am Chem Soc 136:16970

    Article  CAS  Google Scholar 

  9. Quesnel JS, Arndtsen BA (2013) J Am Chem Soc 135:16841

    Article  CAS  Google Scholar 

  10. Fang T, Gao X-H, Tang R-Y, Zhang X-G, Deng C-L (2014) Chem Commun 50:14775

    Article  CAS  Google Scholar 

  11. Gadge ST, Bhanage BM (2014) Org Biomol Chem 12:5727

    Article  CAS  Google Scholar 

  12. Xu T, Alper H (2013) Tetrahedron Lett 54:5496

    Article  CAS  Google Scholar 

  13. Tinnis F, Verho O, Gustafson KPJ, Tai C-W, Bäckvall J-E, Adolfsson H (2014) Chem Eur J 20:5885

    Article  CAS  Google Scholar 

  14. Cai M, Zhao H, Huang Y (2005) J Mol Catal A Chem 238:41

    Article  CAS  Google Scholar 

  15. Hao WY, Sha JC, Sheng SR, Cai MZ (2008) Catal Commun 10:257

    Article  CAS  Google Scholar 

  16. Dang TT, Zhu Y, Ghosh SC, Chen A, Chai CLL, Seayad AM (2012) Chem Commun 48:1805

    Article  CAS  Google Scholar 

  17. Dang TT, Zhu Y, Ngiam JSY, Ghosh SC, Chen A, Seayad AM (2013) ACS Catal 3:1406

    Article  CAS  Google Scholar 

  18. Qureshi ZS, Revankar SA, Khedkar MV, Bhanage BM (2012) Catal Today 198:148

    Article  CAS  Google Scholar 

  19. Islam SM, Ghosh K, Roy AS, Molla RA (2014) RSC Adv 4:38986

    Article  CAS  Google Scholar 

  20. Molla RA, Iqubal MA, Ghosh K, Roy AS, Islam SM (2014) RSC Adv 4:48177

    Article  CAS  Google Scholar 

  21. Li B, Guan Z, Wang W, Yang X, Hu J, Tan B, Li T (2012) Adv Mater 24:3390

    Article  CAS  Google Scholar 

  22. Sun Q, Jiang M, Shen Z, Jin Y, Pan S, Wang L, Meng X, Chen W, Ding Y, Li J, Xiao F-S (2014) Chem Commun 50:11844

    Article  CAS  Google Scholar 

  23. Rose M (2014) ChemCatChem 6:1166

    CAS  Google Scholar 

  24. Zhang Q, Yang Y, Zhang S (2013) Chem Eur J 19:10024

    Article  CAS  Google Scholar 

  25. Jiang M, Yan L, Ding Y, Sun Q, Liu J, Zhu H, Lin R, Xiao F, Jiang Z, Liu J (2015) J Mol Catal A Chem 404–405:211

    Article  Google Scholar 

  26. Sun Q, Dai Z, Liu X, Sheng N, Deng F, Meng X, Xiao F-S (2015) J Am Chem Soc 137:5204

    Article  CAS  Google Scholar 

  27. Lei Y, Wu L, Zhang X, Mei H, Gu Y, Li G (2015) J Mol Catal A Chem 398:164

    Article  CAS  Google Scholar 

  28. Mei H, Hu J, Xiao S, Lei Y, Li G (2014) Appl Catal A Gen 475:40

    Article  CAS  Google Scholar 

  29. Mei H, Xiao S, Zhu T, Lei Y, Li G (2014) Transit Met Chem 39:443

    Article  CAS  Google Scholar 

  30. Barnard CFJ (2008) Org Process Res Dev 12:566

    Article  CAS  Google Scholar 

  31. Genelot M, Villandier N, Bendjeriou A, Jaithong P, Djakovitch L, Dufaud V (2012) Catal Sci Technol 2:1886

    Article  CAS  Google Scholar 

  32. Balogh J, Kuik Á, Ürge L, Darvas F, Bakos J, Skoda-Földes R (2009) J Mol Catal A Chem 302:76

    Article  CAS  Google Scholar 

  33. Takács E, Varga C, Skoda-Földes R, Kollár L (2007) Tetrahedron Lett 48:2453

    Article  Google Scholar 

  34. Papp M, Skoda-Földes R (2013) J Mol Catal A Chem 378:193

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work is partly supported financially by the 863 Program of Ministry of Science and Technology of China (NC2010 MA0137). The authors thank for financial support from the National Natural Science Foundation of China (51504134), Guizhou “125 Plan” Key Project of Science and Technology Project [Qian jiao he zhong da zhuang xiang zi (2013) 026] and Liupanshui normal university creative team (LPSSYKJTD201401).

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Correspondence to Yizhu Lei or Guangxing Li.

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Lei, Y., Zhang, X., Gu, Y. et al. Palladium supported on triphenylphosphine-functionalized porous organic polymer: an efficient heterogeneous catalyst for aminocarbonylation. Transition Met Chem 41, 1–7 (2016). https://doi.org/10.1007/s11243-015-9990-6

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  • DOI: https://doi.org/10.1007/s11243-015-9990-6

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