Skip to main content
Log in

Designing Phase Selectively Soluble Polymer-Supports for Dimethylaminopyridine and Phosphine-Ligated Pd(0) Catalysts

  • Original Paper
  • Published:
Topics in Catalysis Aims and scope Submit manuscript

Abstract

Soluble poly(4-alkylstyrene) containing 4-methyl-, 4-tert-butyl, 4-dodecyl-, and 4-octadecylstyrene were formed either with monomers containing dyes-, ligands, or catalysts or with 5–10 mol% of 4-chloromethylstyrene and studied as supports for ligands or catalysts. Studies with dye-labeled polymers showed that polymers containing longer alkyl groups alone or at ca. 10 mol% loading are highly soluble in heptane can be used to separate and recycle organo- and transition metal catalysts.

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

Access this article

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

Instant access to the full article PDF.

Scheme 1
Scheme 2
Scheme 3
Fig. 1
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Scheme 8
Scheme 9

Similar content being viewed by others

References

  1. Trost BM, Van Vranken DL (1996) Chem Rev 96:395

    Article  CAS  Google Scholar 

  2. Martin R, Buchwald SL (2011) Acc. Chem. Res. 41 (2008) 1461. G. C. Fortman and S. P. Nolan, Chem. Soc. Rev. 40 (2011) 5151. A. Suzuki. Angew Chem Int Ed 50:6722

    Article  Google Scholar 

  3. Hayashi Y, Santoro S, Azuma Y, Himo F, Ohshima T, Mashima K (2013) J Am Chem Soc 135:6192

    Article  CAS  Google Scholar 

  4. Bergbreiter DE, Weatherford DA (1989) J Org Chem 54:2726

    Article  CAS  Google Scholar 

  5. Sieber F, Wentworth P Jr, Toker JD, Wentworth AD, Metz WA, Reed NN, Janda KD (1999) J Org Chem 64:5188

    Article  CAS  Google Scholar 

  6. Zhao L-J, He HS, Shi M, Toy P (2004) J Comb Chem 6:680

    Article  CAS  Google Scholar 

  7. Bergbreiter DE, Yang Y-C, Hobbs CE (2011) J Org Chem 76:6912

    Article  CAS  Google Scholar 

  8. an der Heiden M, Plenio H (2004) Chem Eur J 10:1789

    Article  CAS  Google Scholar 

  9. Collis AEC, Horváth IT (2011) Catal. Sci. Technol. 1:912

    CAS  Google Scholar 

  10. Bergbreiter DE, Li C (2003) Org Lett 5:2445

    Article  CAS  Google Scholar 

  11. Overberger CG, Frazier C, Mandelman J, Smith HF (1953) J Am Chem Soc 75:3326

    Article  CAS  Google Scholar 

  12. Bergbreiter DE, Hughes R, Besinaiz J, Li C, Osburn PL (2003) J Am Chem Soc 125:8244

    Article  CAS  Google Scholar 

  13. Bergbreiter DE, Avilés-Ramos NA, Ortiz-Acosta D (2007) J Comb Chem 9:609

    Article  CAS  Google Scholar 

  14. Clawson RW Jr, Dacko CA, Deavers RE III, Akhmedov NG, Söderberg BCG (2009) Tetrahedron 65:8786

    Article  CAS  Google Scholar 

  15. Khamatnurova TV, Bergbreiter DE (2013) Polym. Chem. 4:1617

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge support by the Qatar National Research Fund (Project Number 4-081-1-016) for the studies of separable Pd(0) catalysts and the Robert A. Welch Foundation (Grant A-0639) for studies of poly(4-alkylstyrene) solubility and its use in organocatalysis. Mr. Jakkrit Suriboot is thanked for his assistance in the ICP-MS analysis of the Pd leaching.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to David E. Bergbreiter.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khamatnurova, T.V., Johnson, M., Santana, D. et al. Designing Phase Selectively Soluble Polymer-Supports for Dimethylaminopyridine and Phosphine-Ligated Pd(0) Catalysts. Top Catal 57, 1438–1444 (2014). https://doi.org/10.1007/s11244-014-0315-3

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11244-014-0315-3

Keywords

Navigation