Skip to main content
SpringerLink
Log in

Synthesis, Characterization of N-Pyrrolylphosphanes Based on Heterocyclic Amine Backbones and Their Application in Hydroformylation of 1-Octene

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

A new class of N-pyrrolylphosphanes based on new heterocyclic amines have been synthesized, characterized and applied in homogeneous rhodium-catalyzed hydroformylation of 1-octene. These ligands possessing strong π-acceptor properties effectively facilitate the olefin isomerization. The steric effect of ligands has also been examined. Large steric tetraphosphane ligand afforded better regioselectivity, and the L/B ratio of about 6.4 was obtained at low synthesis gas pressure (5 bar).

Graphical Abstract

New heterocyclic amines have been developed, and two type pyrrole-based ligands possessing strong π-acceptor and weak ó-donor properties have been prepared. High regioselectivity has been achieved in the rhodium-catalyzed hydroformylation of terminal olefin.

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
Scheme 1

Similar content being viewed by others

References

  1. Trzeciak AM, Ziólkowski JJ (1999) Coord Chem Rev 190:883

    Article  Google Scholar 

  2. Beller M, Cornils B (1995) J Mol Catal A 104:17

    Article  CAS  Google Scholar 

  3. Gonsalvi L, Guerriero A, Monflier E, Peruzzini M (2013) Top Curr Chem 342:1

    Article  CAS  Google Scholar 

  4. Van Leeuwen PWNM, Kamer PCJ, Dierkes P (2000) Chem Rev 100:2741

    Article  Google Scholar 

  5. Casey CP, Whiteker GT, Petrovich LM (1992) J Am Chem Soc 114:5535

    Article  CAS  Google Scholar 

  6. Shibahara F, Nozaki K, Hiyama T (2003) J Am Chem Soc 125:8555

    Article  CAS  Google Scholar 

  7. Kranenburg M, Van der Burgt YEM, Van Leeuwen PWNM (1995) Organometallics 14:3081

    Article  CAS  Google Scholar 

  8. Van der Vlugt JI, Sablong R, Vogt D (2004) Organometallics 23:3177

    Article  Google Scholar 

  9. Vogl C, Paetzold E, Kragl U (2005) J Mol Catal A 232:41

    Article  CAS  Google Scholar 

  10. Selent D, Kreidler B, Börner A (2011) Organometallics 30:4509

    Article  CAS  Google Scholar 

  11. Van der Slot SC, Duran J, Van Leeuwen PWNM (2002) Organometallics 21:3873

    Article  Google Scholar 

  12. Yan YJ, Zhang XW, Zhang XM (2006) J Am Chem Soc 128:16058

    Article  CAS  Google Scholar 

  13. Franke R, Selent D, Börner A (2012) Chem Rev 112:5675

    Article  CAS  Google Scholar 

  14. Jackstell R, Klein H, Beller M (2001) Eur J Org Chem 20:3871

    Article  Google Scholar 

  15. Hamers B, Müller C, Vogt D (2009) ChemCatChem 1:103

    Article  CAS  Google Scholar 

  16. Diebolt O, Tricas H, Van Leeuwen PWNM (2013) ACS Catal 3:128

    Article  CAS  Google Scholar 

  17. Noguchi-Yachide T, Tetsuhashi M (2009) Chem Pharm Bull 57:536

    Article  CAS  Google Scholar 

  18. Dabiri M, Baghbanzadeh M, Azimi SC (2008) Lett Org Chem 5:490

    Article  CAS  Google Scholar 

  19. Yu SC, Dai LY, Zhang XM (2010) Chem Eur J 16:4938

    Article  CAS  Google Scholar 

  20. Zuidema E, Bo C, Van Leeuwen PWNM (2007) Organometallics 26:2234

    Article  CAS  Google Scholar 

  21. Casey CP, Petrovich LM (1995) J Am Chem Soc 117:6007

    Article  CAS  Google Scholar 

  22. Van der Veen LA, Kamer PCJ, Van Leeuwen PWNM (1998) J Am Chem Soc 120:11616

    Article  Google Scholar 

  23. Van der Veen LA, Keeven PH, Van Leeuwen PWNM (2000) Organometallics 19:872

    Article  Google Scholar 

  24. Van Leeuwen PWNM, Kamer PCJ, Reek JNH (1999) Pure Appl Chem 71:1143

    Google Scholar 

  25. Mccleverty JA, Wilkison G (1966) Inorg Synth 8:211

    CAS  Google Scholar 

  26. Bonati F, Wilkison G (1964) J Chem Soc 3156

Download references

Acknowledgment

The authors thank the financial supports from the National Natural Science Foundation of China (201202108).

Author information

Authors and Affiliations

  1. Key Lab of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China

    Lin Zhang, Chun Li, Xueli Zheng, Haiyan Fu, Hua Chen & Ruixiang Li

Authors
  1. Lin Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chun Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xueli Zheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Haiyan Fu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Hua Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ruixiang Li
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hua Chen.

Electronic Supplementary Material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 40 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhang, L., Li, C., Zheng, X. et al. Synthesis, Characterization of N-Pyrrolylphosphanes Based on Heterocyclic Amine Backbones and Their Application in Hydroformylation of 1-Octene. Catal Lett 144, 1074–1079 (2014). https://doi.org/10.1007/s10562-014-1250-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-014-1250-4

Keywords

Search

Navigation