Skip to main content
SpringerLink
Log in

Pillar[5]arene-based N-heterocyclic carbene ligand for Pd-catalysed Suzuki reaction

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

A pillar[5]arene-based N-heterocyclic carbene ligand was prepared by reaction of bromoethoxy pillar[5]arene with excess 1-methylimidazole at 130 °C in the absence of solvent and used as a catalyst for the Suzuki coupling reaction. Excellent yields were obtained when the Suzuki reactions were carried out under ambient atmosphere in ethanol, employing 0.2 mol% ligand, 1 mol% PdCl2(CH3CN)2 and 1.5 mmol of K2CO3. The novel pillar[5]arene-based imidazolium salt is a promising material for the construction of highly active supramolecular catalytic systems.

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
Scheme 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Miyaura, N., Suzuki, A.: Palladium-catalysed cross-coupling reactions of organoboron compounds. Chem. Rev. 95, 2457–2483 (1995)

    Article  CAS  Google Scholar 

  2. Andrus, M.B., Song, C.: Palladium–imidazolium carbene catalysed aryl, vinyl, and alkyl Suzuki–Miyaura cross coupling. Org. Lett. 3, 3761–3764 (2001)

    Article  CAS  Google Scholar 

  3. Bardin, V.V., Shabalin, A.Y., Adonin, N.Y.: Weakly nucleophilic potassium aryltrifluoroborates in palladium-catalysed Suzuki–Miyaura reactions: relative reactivity of K[4-RC6F4BF3] and the role of silver-assistance in acceleration of transmetallation. Beilstein J. Org. Chem. 11, 608–616 (2015)

    Article  CAS  Google Scholar 

  4. Melvin, P.R., Hazari, N., Lant, H.M.C., Peczak, I.L., Shah, H.P.: Comparison of the catalytic activity for the Suzuki–Miyaura reaction of (η5-Cp)Pd(IPr)Cl with (η3-cinnamyl)Pd(IPr)(Cl) and (η3-1-t-Bu-indenyl)Pd(IPr)(Cl). Beilstein J. Org. Chem. 11, 2476–2486 (2015)

    Article  CAS  Google Scholar 

  5. Akkoç, S., Gök, Y., İlhan, İ.Ö., Kayser, V.: N-Methylphthalimide-substituted benzimidazolium salts and PEPPSI Pd–NHC complexes: synthesis, characterization and catalytic activity in carbon–carbon bond-forming reactions. Beilstein J. Org. Chem. 12, 81–88 (2016)

    Article  Google Scholar 

  6. Wang, S., Wang, Y., Chen, Z., Lin, Y., Weng, L., Han, K., Li, J., Jia, X., Li, C.: The marriage of endo-cavity and exo-wall complexation provides a facile strategy for supramolecular polymerization. Chem. Commun. 51, 3434–3437 (2015)

    Article  CAS  Google Scholar 

  7. Arduengo, A.J., Harlow, R.L., Kline, M.: A stable crystalline carbene. J. Am. Chem. Soc. 113(1), 361–363 (1991)

    Article  CAS  Google Scholar 

  8. Ramgren, S.D., Hie, L., Ye, Y., Garg, N.K.: Nickel-catalysed Suzuki–Miyaura couplings in green solvents. Org. Lett. 15, 3950–3953 (2013)

    Article  CAS  Google Scholar 

  9. Nelson, D.J., Collado, A., Manzini, S., Meiries, S., Slawin, A.M.Z., Cordes, D.B., Nolan, S.P.: Methoxy-functionalized N-heterocyclic carbenes. Organometallics 33, 2048–2058 (2014)

    Article  CAS  Google Scholar 

  10. Menon, R.S., Biju, A.T., Nair, V.: Recent advances in N-heterocyclic carbene (NHC)-catalysed benzoin reactions. Beilstein J. Org. Chem. 12, 444–461 (2016)

    Article  CAS  Google Scholar 

  11. Gómez-Suárez, A., Oonishi, Y., Martin, A.R., Nolan, S.P.: Scope and limitations of the dual-gold-catalysed hydrophenoxylation of alkynes. Beilstein J. Org. Chem. 12, 172–178 (2016)

    Article  Google Scholar 

  12. Cacciapaglia, R., Di Stefano, S., Mandolini, L.: The bis-barium complex of a butterfly crown ether as a phototunable supramolecular catalyst. J. Am. Chem. Soc. 125, 2224–2227 (2003)

    Article  CAS  Google Scholar 

  13. Sharghi, H., Massah, A.R., Eshghi, H., Niknam, K.: Crown ethers as new catalysts in the highly regioselective halogenative cleavage of epoxides with elemental halogen. J. Org. Chem. 63, 1455–1461 (1998)

    Article  CAS  Google Scholar 

  14. Stuart, A.M., Vidal, J.A.: Perfluoroalkylated 4,13-diaza-18-crown-6 ethers:  synthesis, phase-transfer catalysis, and recycling studies. J. Org. Chem. 72, 3735–3740 (2007)

    Article  CAS  Google Scholar 

  15. Leclercq, L., Schmitzer, A.R.: Assembly of tunable supramolecular organometallic catalysts with cyclodextrins. Organometallics 29, 3442–3449 (2010)

    Article  CAS  Google Scholar 

  16. Cassez, A., Ponchel, A., Hapiot, F., Monflier, E.: Unexpected multifunctional effects of methylated cyclodextrins in a palladium charcoal-catalysed Suzuki–Miyaura reaction. Org. Lett. 8, 4823–4826 (2006)

    Article  CAS  Google Scholar 

  17. Notestein, J.M., Iglesia, E., Katz, A.: Grafted Metallocalixarenes as Single-Site Surface Organometallic Catalysts. J. Am. Chem. Soc. 126, 16478–16486 (2004)

    Article  CAS  Google Scholar 

  18. Meninno, S., Parrella, A., Brancatelli, G., Geremia, S., Gaeta, C., Talotta, C., Neri, P., Lattanzi, A.: Polyoxomolybdate-calix[4]arene hybrid: a catalyst for sulfoxidation reactions with hydrogen peroxide. Org. Lett. 17, 5100–5103 (2015)

    Article  CAS  Google Scholar 

  19. Fantauzzi, S., Gallo, E., Rose, E., Raoul, N., Caselli, A., Issa, S., Ragaini, F., Cenini, S.: Asymmetric cyclopropanation of olefins catalysed by chiral cobalt(II)-binaphthyl porphyrins. Organometallics 27, 6143–6151 (2008)

    Article  CAS  Google Scholar 

  20. Ferrand, Y., Le Maux, P., Simonneaux, G.: Highly enantioselective synthesis of cyclopropylphosphonates catalysed by chiral ruthenium porphyrins. Org. Lett. 6, 3211–3214 (2004)

    Article  CAS  Google Scholar 

  21. Zhang., X., Qiu, Y., Rao, B., Luo, M.: Palladium(II)–N-heterocyclic carbene metallacrown ether complexes: synthesis, structure, and catalytic activity in the Suzuki–Miyaura reaction. Organometallics 28, 3093–3099 (2009)

    Article  CAS  Google Scholar 

  22. Wang, J.W., Meng, F.H., Zhang, L.F.: Suzuki coupling reaction of aryl halides catalysed by an N-heterocyclic carbene–PdCl2 species based on a porphyrin at room temperature. Organometallics 28, 2334–2337 (2009)

    Article  CAS  Google Scholar 

  23. Wang, J.W., Gao, L.Y., Meng, F.H., Jiao, J., Ding, L.Y., Zhang, L.F.: Synthesis, characterization of N-heterocyclic carbene metallacrown palladium complex and catalytic activities in Suzuki and Heck coupling reaction. J. Incl. Phenom. Macrocycl. Chem. 73, 119–128 (2011)

    Article  Google Scholar 

  24. Ren, H., Xu., Y., Jeanneau, E., Bonnamour, I., Tu, T., Darbost, U.: Synthesis, characterization and X-ray structures of N-heterocyclic carbene palladium complexes based on calix[4]arenes: highly efficient catalysts towards Suzuki–Miyaura cross-coupling reactions. Tetrahedron 70, 2829–2837 (2014)

    Article  CAS  Google Scholar 

  25. Ogoshi, T., Kanai, S., Fujinami, S., Yamagishi, T.A., Nakamoto, Y.: para-Bridged symmetrical pillar[5]arenes: their lewis acid catalysed synthesis and host–guest property. J. Am. Chem. Soc. 130, 5022–5023 (2008)

    Article  CAS  Google Scholar 

  26. Ogoshi, T., Yamagishi, T.-A., Nakamoto, Y.: Pillar-shaped macrocyclic hosts Pillar[n]arenes: new key players for supramolecular chemistry. Chem. Rev. 116, 7937–8002 (2016)

    Article  CAS  Google Scholar 

  27. Ogoshi, T., Ueshima, N., Yamagishi, T.A., Toyota, Y., Matsumi, N.: Ionic liquid pillar[5]arene: its ionic conductivity and solvent-free complexation with a guest. Chem. Commun. 48, 3536–3538 (2012)

    Article  CAS  Google Scholar 

  28. Yao, Y., Xue, M., Chi, X., Ma, Y., He, J., Abliz, Z., Huang, F.: A new water-soluble pillar[5]arene: synthesis and application in the preparation of gold nanoparticles. Chem. Commun. 48, 6505–6507 (2012)

    Article  CAS  Google Scholar 

  29. Wang, J.W., Li, Q.S., Xu, F.B., Song, H.B., Zhang., Z.Z.: Synthetic and structural studies of silver(I)- and gold(I)-containing N-heterocyclic carbene metallacrown ethers. Eur. J. Org. Chem. 2006, 1310–1316 (2006)

    Article  Google Scholar 

  30. Cao, R., McCarthy, B.D., Lippard, S.J.: Immobilization, trapping, and anion exchange of perrhenate ion using copper-based tripodal complexes. Inorg. Chem. 50, 9499–9507 (2011)

    Article  CAS  Google Scholar 

  31. Mu., B., Li, J., Han, Z., Wu, Y.: Fast Suzuki–Miyaura cross-coupling reaction catalysed by the Na2Pd2Cl6 complex with ethyl calix[4]aryl acetate at room temperature in aqueous medium under ligand-free and ambient atmosphere. J. Organomet. Chem. 700, 117–124 (2012)

    Article  CAS  Google Scholar 

  32. Zhao, G., Wang, Z., Wang, R., Li, J., Zou, D., Wu, Y.: Cucurbit[7]uril promoting PdCl2-catalysed cross-coupling reaction of benzyl halides and arylboronic acids in aqueous media. Tetrahedron Lett. 55, 5319–5322 (2014)

    Article  CAS  Google Scholar 

  33. Cao., M., Wei, Y., Gao, S., Cao, R.: Synthesis of palladium nanocatalysts with cucurbit[n]uril as both a protecting agent and a support for Suzuki and Heck reactions. Catal. Sci. Technol. 2, 156–163 (2012)

    Article  CAS  Google Scholar 

  34. Zhao, Y., Liang, L.L., Chen, K., Ji., N.N., Cheng, X.J., Xiao, X., Zhang, Y.Q., Xue, S.F., Zhu, Q.J., Dong, N., Tao, Z.: [CdCl4]2− anion-induced coordination of alkaline earth metal ions to cucurbit[7]uril, corresponding supramolecular self-assemblies and potential application. Dalton T. 43, 929–932 (2014)

    Article  CAS  Google Scholar 

  35. Ong, W., Kaifer, A.E.: Salt effects on the apparent stability of the cucurbit[7]uril–methyl viologen inclusion complex. J. Org. Chem. 69, 1383–1385 (2004)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We are grateful for the support provided by the Research Fund for the Shanxi Natural Science Foundation of China for the Project (No. 2011011006-4).

Author information

Authors and Affiliations

  1. Department of Chemistry, Shanxi Normal University, Linfen, 041004, People’s Republic of China

    Xue-Dong Xiao, Jia-Qi Liu, Ya-Li Bai, Rui-Hua Wang & Jun-Wen Wang

Authors
  1. Xue-Dong Xiao
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jia-Qi Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ya-Li Bai
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Rui-Hua Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jun-Wen Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jun-Wen Wang.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1011 kb)

Supplementary data (1H NMR, 13C NMR and IR spectra for compounds) associated with this article can be found

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Xiao, XD., Liu, JQ., Bai, YL. et al. Pillar[5]arene-based N-heterocyclic carbene ligand for Pd-catalysed Suzuki reaction. J Incl Phenom Macrocycl Chem 87, 29–36 (2017). https://doi.org/10.1007/s10847-016-0673-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-016-0673-5

Keywords

Search

Navigation