Skip to main content
Log in

Effective C–O Bond Cleavage of Lignin β-O-4 Model Compounds: A New RuHCl(CO)(PPh3)3/KOH Catalytic System

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Base, especially KOH, can be used in place of xantphos for the Ruthenium-complex-catalyzed C–O bond cleavage of β-O-4 lignin model compounds. In the presence of KOH, RuHCl(CO)(PPh3)3 and Ru(H)2(CO)(PPh3)3 show the best catalytic effect among several ruthenium-complexes studied.

Graphical Abstract

Base, especially KOH, can be used in place of xantphos for the Ruthenium-complex-catalyzed C–O bond cleavage of β-O-4 lignin model compounds. In the presence of KOH, RuHCl(CO)(PPh3)3 and Ru(H)2(CO)(PPh3)3 show the best catalytic effect among several ruthenium-complexes studied.

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.

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Corma A, Iborra S, Velty A (2007) Chem Rev 107:2411–2502

    Article  CAS  Google Scholar 

  2. Dodds DR, Gross RA (2007) Science 318:1250–1251

    Article  CAS  Google Scholar 

  3. Lai YZ, Sarkanen KV (1971) Isolation and structural studies. In: Sarkanen KV, Ludwig CH (eds) Lignins: Occurrence, Formation, Structure and Reactions. Wiley-Interscience, New York, pp 195–230

    Google Scholar 

  4. Adam W, Patrick BO, Chung E, James BR (2012) Dalton Trans 41:11093

    Article  Google Scholar 

  5. Regalbuto JR (2009) Science 325:822

    Article  Google Scholar 

  6. Cho DW, Latham JA, Park HJ, Yoon UC, Langan P, Dunaway-Mariano D, Mariano PS (2011) J Org Chem 76:2840–2852

    Article  CAS  Google Scholar 

  7. Ohlrogge J, Allen D, Berguson B, DellaPenna D, Shachar-Hill Y, Stymne S (1019) Science 2009:324

    Google Scholar 

  8. Brown ME, Walker MC, Nakashige TG, Iavarone AT, Chang MCY (2011) J Am Chem Soc 133:18006

    Article  CAS  Google Scholar 

  9. Badamali SK, Luque R, Clark JH, Breeden SW (2011) Catal Commun 12:993

    Article  CAS  Google Scholar 

  10. Jia S, Cox BJ, Guo X, Zhang ZC, Ekerdt JG (2011) Ind Eng Chem Res 50:849

    Article  CAS  Google Scholar 

  11. Song Qi, Wang Feng, Cai Jiaying, Wang Yehong, Zhang Junjie, Yua Weiqiang, Jie Xu, (2013) Environ Energy Sci 6:994–1007

    Article  CAS  Google Scholar 

  12. Chan JMW, Bauer S, Sorek H, Sreekumar S, Wang K, Toste D (2013) ACS Catal 3:1369–1377

    Article  CAS  Google Scholar 

  13. Son S, Toste FD (2010) Angew Chem Int Ed 49:3791–3794

    Article  CAS  Google Scholar 

  14. Nichols JM, Bishop LM, Bergman RG, Ellman JA (2010) J Am Chem Soc 132:12554–12555

    Article  CAS  Google Scholar 

  15. Kamer PCJ, Van Leeuwen PWNM, Reek JNH (2001) Acc Chem Res 34:895–904

    Article  CAS  Google Scholar 

  16. Gierer J, Kunze I (1961) Acta Chem Scand 15:803

    Article  CAS  Google Scholar 

  17. Gierer J, Noren I (1962) Acta Chem Scand 16:1976

    Article  CAS  Google Scholar 

  18. Mizushima Eiichiro, Yamaguchi Motowo, Yamagishi Takamichi (1999) J Mol Catal A 148:69–75

    Article  CAS  Google Scholar 

  19. Aranyos A, Csjernyik G, Szabo KJ, Backvall JE (1999) Chem Commun 4:351–352

    Article  Google Scholar 

  20. Douglas, P. G, Shaw, B. L (1970) J Chem Soc A 1556–1557

  21. Coe BJ, Glenwright SJ (2000) Coord Chem Rev 203:5

    CAS  Google Scholar 

Download references

Acknowledgments

The research project is financially supported by the National Natural Science Foundation of China (51176184), the National Basic Research Program of China (No. 2012CB215302), the National High-tech R&D Program (2012AA101808-2), and by the Fundamental Research Funds for the Central Universities (WK2090130009).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Wenzhi Li.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 2738 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Huo, W., Li, W., Zhang, M. et al. Effective C–O Bond Cleavage of Lignin β-O-4 Model Compounds: A New RuHCl(CO)(PPh3)3/KOH Catalytic System. Catal Lett 144, 1159–1163 (2014). https://doi.org/10.1007/s10562-014-1264-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-014-1264-y

Keywords

Navigation