Skip to main content
SpringerLink
Log in

Diphosphino-Functionalized MCM-41-Immobilized Rhodium Complex: A Highly Efficient and Recyclable Catalyst for the Hydrophosphinylation of Terminal Alkynes

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Diphosphino-functionalized MCM-41-immobilized rhodium complex (MCM-41-2P-RhCl3) was conveniently synthesized from commercially available and cheap γ-aminopropyltriethoxysilane via immobilization on mesoporous MCM-41, followed by reacting with diphenylphosphinomethanol and rhodium chloride. It was found that this heterogeneous rhodium complex is a highly efficient catalyst for the hydrophosphinylation of terminal alkynes with diphenylphosphine oxide and can be recovered and recycled by a simple filtration of the reaction solution and used for at least 10 consecutive trials without any decreases in activity.

Graphical Abstract

Hydrophosphinylation of terminal alkynes using diphosphino-functionalized MCM-41-immobilized rhodium complex (MCM-41-2P-RhCl3) as an efficient heterogeneous catalyst is described. This heterogeneous rhodium complex is highly active catalyst and can be reused at least 10 times without any decrease in activity.

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

Scheme 1
Fig. 1
Scheme 2

Similar content being viewed by others

References

  1. Niu M, Fu H, Jiang Y, Zhao Y (2007) Chem Commun 272

  2. Inoue H, Nagaoka Y, Tomioka K (2002) J Org Chem 67:5864

    Article  CAS  Google Scholar 

  3. Rahman MS, Oliana M, Hii KK (2004) Tetrahedron Asymmetr 15:1835

    Article  CAS  Google Scholar 

  4. Barbaro P, Bianchini C, Giambastiani G, Togni A (2002) Chem Commun 2672

  5. Han L-B, Zhao C-Q (2005) J Org Chem 70:10121

    Article  CAS  Google Scholar 

  6. Nicolaou KC, Maligres P, Shin J, de Leon E, Rideout D (1990) J Am Chem Soc 112:7825

    Article  CAS  Google Scholar 

  7. Johnson CR, Imamoto T (1987) J Org Chem 52:2170

    Article  CAS  Google Scholar 

  8. Pietrusiewicz KM, Wisniewski W, Zablocka M (1989) Tetrahedron 45:337

    Article  CAS  Google Scholar 

  9. Pietrusiewicz KM, Zablocka M (1988) Tetrahedron Lett 29:1991

    Article  CAS  Google Scholar 

  10. Brunner H, Limmer S (1991) J Organomet Chem 417:173

    Article  CAS  Google Scholar 

  11. Cavalla D, Warren S (1982) Tetrahedron Lett 23:4505

    Article  CAS  Google Scholar 

  12. Brunner H, Limmer S (1991) J Organomet Chem 413:55

    Article  CAS  Google Scholar 

  13. Pietrusiewicz KM, Zablocka M (1988) Tetrahedron Lett 29:937

    Article  CAS  Google Scholar 

  14. Keck GE, Byers JH, Tafesh AM (1988) J Org Chem 53:1127

    Article  CAS  Google Scholar 

  15. Brandi A, Cicchi S, Goti A (1991) Tetrahedron Lett 32:3265

    Article  CAS  Google Scholar 

  16. Han L-B, Mirzael F, Zhao C-Q, Tanaka M (2000) J Am Chem Soc 122:5407

    Article  CAS  Google Scholar 

  17. Zhao C-Q, Han L-B, Tanaka M (2000) Organometallics 19:4196

    Article  CAS  Google Scholar 

  18. Zhao C-Q, Han L-B, Coto M, Tanaka M (2001) Angew Chem Int Ed 40:1929

    Article  CAS  Google Scholar 

  19. Han L-B, Hua R, Tanaka M (1998) Angew Chem Int Ed 37:94

    Article  CAS  Google Scholar 

  20. Han L-B, Zhang C, Yazawa H, Shimada S (2004) J Am Chem Soc 126:5080

    Article  CAS  Google Scholar 

  21. Han L-B, Zhao C-Q, Tanaka M (2001) J Org Chem 66:5929

    Article  CAS  Google Scholar 

  22. Iwasawa Y (1986) Tailored metal catalysts. Reidel D Publishing Company, Dordrecht

    Google Scholar 

  23. Poliakoff M, Fitzpatrick JM, Farren TR, Anastas PT (2002) Science 297:807

    Article  CAS  Google Scholar 

  24. Kirschnig A, Monenschein H, Wittenberg R (2001) Angew Chem Int Ed 40:650

    Article  Google Scholar 

  25. Sander AJ, Reek JNH, Kamer PCJ, van Leeuwen PWNM (2001) J Am Chem Soc 123:8468

    Article  Google Scholar 

  26. Merckle C, Blumel J (2003) Adv Synth Catal 345:584

    Article  CAS  Google Scholar 

  27. Zhou W, He DH (2009) Green Chem 11:1146

    Article  CAS  Google Scholar 

  28. Bourque SC, Mlatais F, Xiao WJ, Tardif O, Alper H, Arya P, Manzer LE (1999) J Am Chem Soc 121:3035

    Article  CAS  Google Scholar 

  29. Marras F, Wang J, Coppens MO, Reek JNH (2010) Chem Commun 46:6587

    Article  CAS  Google Scholar 

  30. Sayah R, Framery E, Dufaud V (2009) Green Chem 11:1694

    Article  CAS  Google Scholar 

  31. Marciniec B, Szubert K, Fiedorow R, Kownacki I, Potrzebowski MJ, Dutkiewicz M, Franczyk A (2009) J Mol Catal A Chem 310:9

    Article  CAS  Google Scholar 

  32. Balcar H, Sedlacek J, Cejka J, Vohlidal J (2002) Macromol Rapid Commun 23:32

    Article  CAS  Google Scholar 

  33. Yang Y, Rioux RM (2011) Chem Commun 47:6557

    Article  CAS  Google Scholar 

  34. Kresge CT, Leonowicz ME, Roth WJ, Vartuli JC, Beck JS (1992) Nature 359:710

    Article  CAS  Google Scholar 

  35. Taguchi A, Schuth F (2005) Micropor Mesopor Mater 77:1

    Article  CAS  Google Scholar 

  36. Martin-Aranda RM, Cejka J (2010) Top Catal 53:141

    Article  CAS  Google Scholar 

  37. Beck JS, Vartuli JC, Roth WJ, Leonowicz ME, Kresge CT, Schmitt KD, Chu CT-W, Olson DH, Sheppard EW, McCullen SB, Higgins JB, Schlenker JL (1992) J Am Chem Soc 114:10834

    Article  CAS  Google Scholar 

  38. Zhou W, Thomas JM, Shephard DS, Johnson BFG, Ozkaya D, Maschmeyer T, Bell RG, Ge Q (1998) Science 280:705

    Article  CAS  Google Scholar 

  39. Maschmeyer T, Rey F, Sankar G, Thomas JM (1995) Nature 378:159

    Article  CAS  Google Scholar 

  40. Liu C-J, Li S-G, Pang W-Q, Che C-M (1997) Chem Commun 65

  41. Shyu S-G, Cheng S-W, Tzou D-L (1999) Chem Commun 2337

  42. Lim MH, Stein A (1999) Chem Mater 11:3285

    Article  CAS  Google Scholar 

  43. Han L-B, Chol N, Tanaka M (1996) Organometallics 15:3259

    Article  CAS  Google Scholar 

  44. Lempers HEB, Sheldon RA (1998) J Catal 175:62

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge the financial support of this work by the National Natural Science Foundation of China (Project No. 20862008) and the Natural Science Foundation of Jiangxi Province in China (Project No. 2010GZH0062).

Author information

Authors and Affiliations

  1. Department of Chemistry, Jiangxi Normal University, Nanchang, 330022, People’s Republic of China

    Fang Yao, Jian Peng, Wenyan Hao & Mingzhong Cai

  2. Department of Chemistry and Pharmaceutical Engineering, West Branch of Zhejiang University of Technology, Quzhou, 324000, People’s Republic of China

    Fang Yao

Authors
  1. Fang Yao
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jian Peng
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Wenyan Hao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mingzhong Cai
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mingzhong Cai.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yao, F., Peng, J., Hao, W. et al. Diphosphino-Functionalized MCM-41-Immobilized Rhodium Complex: A Highly Efficient and Recyclable Catalyst for the Hydrophosphinylation of Terminal Alkynes. Catal Lett 142, 803–808 (2012). https://doi.org/10.1007/s10562-012-0781-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-012-0781-9

Keywords

Search

Navigation