Skip to main content

Advertisement

SpringerLink
Log in

Mesoporous Carbon Supporting Pd (0) as a Highly Efficient and Stable Catalyst for Sonogashira Reaction in Aqueous Media

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

In this study, palladium (0) nanoparticle supported on mesoporous carbon (Pd/MPC) is prepared by impregnation and H2 reduction. Characterization by XRD, XPS and TEM reveals the mesoporous structure and a high dispersion of palladium nanoparticles (about 4.8 nm) in the mesopores. The catalyst has excellent catalytic activity and stability for Sonogashira reactions of aryl halide (–I, –Br) in aqueous solution. It is noteworthy that Sonogashira reactions of aryl halide (–Cl) can occur by using the novel Pd/MPC catalyst. Meanwhile, the catalyst can be recovered and reused without loss of efficiency until the fifth cycle in water. The fresh catalyst would be of major significance for industrial applications.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Sakai N, Annaka K, Konakahara T (2004) Palladium-catalyzed coupling reaction of terminal alkynes with aryl iodides in the presence of indium tribromide and its application to a one-pot synthesis of 2-phenylindole. Org Lett 6:1527–1530

    Article  CAS  Google Scholar 

  2. Liang Y, Xie YX, Li JH (2006) Modified palladium-catalyzed Sonogashira cross-coupling reactions under copper-, amine-, and solvent-free conditions. J Org Chem 71:379–381

    Article  CAS  Google Scholar 

  3. Huang H, Liu H, Jiang HL, Chen KX (2008) Rapid and efficient Pd-catalyzed Sonogashira coupling of aryl chlorides. J Org Chem 73:6037–6040

    Article  CAS  Google Scholar 

  4. Hajipour AR, Fatemeh R (2014) (BeDABCO)2Pd2Cl6 as an efficient homogeneous catalyst for copper-free Sonogashira cross-coupling reaction. Appl Organomet Chem 28:595–597

    Article  CAS  Google Scholar 

  5. Ranjan VP, Soumik M, Parna G, Balaram M (2013) Carbohydrate derived thiosemicarbazone and semicarbazone palladium complexes: homogeneous catalyst for C–C cross coupling reactions. Tetrahedron Lett 54:4914–4917

    Article  Google Scholar 

  6. Lipshutz BH, Chung DW, Rich B (2008) Sonogashira couplings of aryl bromides: room temperature, water only, no copper. Org Lett 10:3793–3796

    Article  CAS  Google Scholar 

  7. Arhancet JP, Davis ME, Merola JS, Hanson BE (1989) Hydroformylation by supported aqueous-phase catalysis: a new class of heterogeneous catalysts. Nature 339:454

    Article  CAS  Google Scholar 

  8. Bhunia S, Sen R, Koner S (2010) Anchoring of palladium(II) in chemically modified mesoporous silica: an efficient heterogeneous catalyst for Suzuki cross-coupling reaction. Inorg Chim Acta 363:3993–3999

    Article  CAS  Google Scholar 

  9. Parshina LN, Tantsyrev AP, Grishchenko LA, Trofimov BA (2013) Nanosized Pd(0)-arabinogalactan composites as catalysts in the Sonogashira reaction. Russ J Org Chem 49:412–416

    Article  CAS  Google Scholar 

  10. Zeng MF, Qi CZ, Yang J, Wang BY, Zhang XM (2014) A highly efficient and stable palladium catalyst entrapped with in the cross-linked chitosan membrane for Heck reactions. Ind Eng Chem Res 53:10041–10050

    Article  CAS  Google Scholar 

  11. Miran K, Hyuntae K, Park KH (2015) Pd nanoparticles supported on Fe3O4@amine-functionalized graphene composite and catalytic performance in Sonogashira cross-coupling reactions. Catal Commun 72:150–155

    Article  Google Scholar 

  12. Suzana N, Raed BR (2015) Functionalized magnetic mesoporous silica nanoparticle-supported palladium catalysts for carbonylative Sonogashira coupling reactions of aryl iodides. ChemCatChem 7:2230–2240

    Article  Google Scholar 

  13. Feng YS, Lin XY, Hao J, Xu HJ (2014) Pd–Co bimetallic nanoparticles supported on graphene as a highly active catalyst for Suzuki–Miyaura and Sonogashira cross-coupling reactions. Tetrahedron 70:5249

    Article  CAS  Google Scholar 

  14. Basavaprabhu, Samarasimhareddy M, Girish P, Sureshbabu VV (2014) A simple and greener approach for the synthesis of PVC supported Pd(0): application to Heck and Sonogashira reactions in water. Tetrahedron Lett 55:2256–2260

    Article  CAS  Google Scholar 

  15. Jana S, Dutta B, Bera R, Koner S (2008) Immobilization of palladium in mesoporous silica matrix: preparation, characterization, and its catalytic efficacy in carbon–carbon coupling reactions. Inorg Chem 47:5512–5520

    Article  CAS  Google Scholar 

  16. Zhang FQ, Meng Y, Gu D, Yan Y, Yu CZ, Tu B, Zhao DY (2005) A facile aqueous route to synthesize highly ordered mesoporous polymers and carbon frameworks with Ia3hd bicontinuous cubic structure. J Am Chem Soc 127:13508–13509

    Article  CAS  Google Scholar 

  17. Meng Y, Gu D, Zhang FQ (2006) A family of highly ordered mesoporous polymer resin and carbon structures from organic–organic self-assembly. Chem Mater 18:4447–4464

    Article  CAS  Google Scholar 

  18. Schaetz A, Zeltner M, Stark JW (2012) Carbon modifications and surfaces for catalytic organic transformations. ACS Catal 2:1267–1284

    Article  CAS  Google Scholar 

  19. Mohammad B, Saeideh J (2013) Pd/C-catalyzed, copper-free Sonogashira coupling: one-pot synthesis of 1-aryl-4-(2-phenylethynyl)[1,2,4]triazolo[4,3-a] quinoxalines in water. Monatsh Chem 144:885–890

    Article  Google Scholar 

  20. Dai LM, Chang D, Lu W (2012) Carbon nanomaterials for advanced energy conversion and storage. Small 8:1130–1166

    Article  CAS  Google Scholar 

  21. Li Y, Fan XB, Qi JJ, Ji JY, Wang SL, Zhang GL et al (2010) Palladium nanoparticle–graphene hybrids as active catalysts for the Suzuki reaction. Nano Res 3:429–437

    Article  CAS  Google Scholar 

  22. Guo SJ, Dong SJ, Wang EW (2010) Three-dimensional Pt-on-Pd bimetallic nanodendrites supported on graphene nanosheet: facile synthesis and used as an advanced nanoelletrocatalyst forme than oloxidation. ACS Nano 4:547–555

    Article  CAS  Google Scholar 

  23. Yoo E, Okata T, Akita T et al (2009) Enhanced electrocatalytic activity of Pt subnanoclusters on graphene nanosheet surface. Nano Lett 9:2255–2259

    Article  CAS  Google Scholar 

  24. Wen Z, Wang X, Mao S, Bo Z, Kim H, Cui S, Lu G, Feng X, Chen J (2012) Crumpled nitrogen-doped graphene nanosheets with ultrahigh pore volume for high-performance supercapacitor. Adv Mater 24:5610

    Article  CAS  Google Scholar 

  25. Siamaki AR, Lin B, Woodberry K, Connell JW, Gupton BF (2013) Palladium nanoparticles supported on carbon nanotubes from solventless preparations: versatile catalysts for ligand-free Suzuki cross coupling reactions. J Mater Chem A 1:12909–12918

    Article  CAS  Google Scholar 

  26. Cheng L, Hong S, Zhou X, Zhou Z, Hou H (2008) Novel Pd-carrying composite carbon nanofibers based on polyacrylonitrile as a catalyst for Sonogashira coupling reaction. Catal Commun 9:2221–2225

    Article  Google Scholar 

  27. Li W, Zhang F, Dou Y, Wu Z, Liu H, Qian X, Gu D, Xia Y, Tu B, Zhao D (2011) A new family of carbon materials: synthesis of MOF-derived nanoporous carbons and their promising applications. Adv Energy Mater 1:382

    Article  CAS  Google Scholar 

  28. Wan Y, Wang HY, Zhao QF, Klingstedt M, Terasaki O, Zhao DY (2009) Ordered mesoporous Pd/silica–carbon as a highly active heterogeneous catalyst for coupling reaction of chlorobenzene in aqueous media. J Am Chem Soc 131:4541–4550

    Article  CAS  Google Scholar 

  29. Handa P, Wikander K, Holmberg K (2009) The Sonogashira reaction catalyzed by palladium leached from ordered mesoporous carbon. Microporous Mesoporous Mater 117:126–135

    Article  CAS  Google Scholar 

  30. Pikna L, Milkoviča O, Saksl K, Heželová M, Smrčová M, Puliša P, Michalik S, Gamcová J (2014) The structure of nano-palladium deposited on carbon-based supports. J Solid State Chem 212:197–204

    Article  CAS  Google Scholar 

  31. Xu X, Li Y, Gong YT, Zhang PF (2012) Synthesis of palladium nanoparticles supported on mesoporous N-doped carbon and their catalytic ability for biofuel upgrade. J Am Chem Soc 134:16987–16990

    Article  CAS  Google Scholar 

  32. Chen XY, Chen C, Zhang ZJ, Xie DH (2013) A general approach for producing nanoporous carbon especially evinced in the case of adipic acid and zinc. J Mater Chem A 1:14919–14926

    Article  CAS  Google Scholar 

  33. Ryoo R, Joo SH, Jun S (1999) Synthesis of highly ordered carbon molecular sieves via template-mediated structural transformation. J Phys Chem B 103:37

    Google Scholar 

  34. Peter C, Derible A, Becht JM (2015) Biosourced mesoporous carbon with embedded palladium nanoparticles by a one pot soft-template synthesis: application to Suzuki reactions. J Mater Chem A 3:12297

    Article  CAS  Google Scholar 

  35. Kim SW, Park J, Jang Y, Chung Y, Hwang S, Hyeon T (2003) Synthesis of monodisperse palladium nanoparticles. Nano Lett 3:1289–1291

    Article  CAS  Google Scholar 

  36. Bhunia S, Koner S (2011) Heterogeneous Stille and Sonogashira cross-coupling reactions over palladium anchored mesoporous silica catalyst. Indian J Chem 50A:1380–1387

    CAS  Google Scholar 

  37. Polshettiwar V, Molnar A (2007) Silica-supported Pd catalysts for Heck coupling reactions. Tetrahedron 63:6949

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We gratefully acknowlege financial assistance from the National Natural Science Foundation of China (Nos. 21371044, 21571047) and the Program for New Century Excellent Talents in University of the Chinese Ministry of Education(NCET-11-0627).

Author information

Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Hefei University of Technology, 193 Tunxi Road, Hefei, 230009, China

    Peng Wang, Guang-Yu Wang, Wen-Long Qiao & Yi-Si Feng

  2. Controllable Chemical Engineering and Materials Chemical Engineering of Anhui Key Laboratory, 193 Tunxi Road, Hefei, 230009, China

    Peng Wang, Guang-Yu Wang, Wen-Long Qiao & Yi-Si Feng

  3. Anhui Provincial Laboratory of Heterocyclic Chemistry, 193 Tunxi Road, Hefei, 230009, China

    Peng Wang, Guang-Yu Wang, Wen-Long Qiao & Yi-Si Feng

Authors
  1. Peng Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Guang-Yu Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Wen-Long Qiao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yi-Si Feng
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yi-Si Feng.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 3545 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wang, P., Wang, GY., Qiao, WL. et al. Mesoporous Carbon Supporting Pd (0) as a Highly Efficient and Stable Catalyst for Sonogashira Reaction in Aqueous Media. Catal Lett 146, 1792–1799 (2016). https://doi.org/10.1007/s10562-016-1803-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-016-1803-9

Keywords

Search

Navigation