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Hydrogenolysis of a γ-Acetylated Lignin Model Compound with a Ruthenium–Xantphos Catalyst

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Abstract

Catalytic hydrogenolysis of a γ-acetylated dimer lignin model compound is effected using a Ru–xantphos catalyst. Mechanistic investigations show mono-aryl degradation products are generated from the β-O-4 substrate as well as a terminal alkene ketone dimer (bis-aryl) that further dimerizes to a tetra-aryl product. Preliminary results using an acetylated kraft lignin as a substrate are also discussed.

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References

  1. Thilakaratne R, Brown T, Li YH, Hu GP, Brown R (2014) Green Chem 16:627

    Article  CAS  Google Scholar 

  2. Saha B, Abu-Omar MM (2014) Green Chem 16:24

    Article  CAS  Google Scholar 

  3. Osatiashtiani A, Lee AF, Brown DR, Melero JA, Morales G, Wilson K (2014) Catal Sci Technol 4:333

    Article  CAS  Google Scholar 

  4. Rahimi A, Azarpira A, Kim H, Ralph J, Stahl SS (2013) J Am Chem Soc 135:6415

    Article  CAS  Google Scholar 

  5. Heracleous E, Lemonidou A (2013) Platinum Met Rev 57:101

    Article  Google Scholar 

  6. Hanson SK, Wu R, Silks LAP (2012) Angew Chem. Int Ed 51:3410

    Article  CAS  Google Scholar 

  7. Azadi P, Carrasquillo-Flores R, Pagan-Torres YJ, Gurbuz EI, Farnood R, Dumesic JA (2012) Green Chem 14:1573

    Article  CAS  Google Scholar 

  8. Collinson SR, Thielemans W (2010) Coord Chem Rev 254:1854

    Article  CAS  Google Scholar 

  9. Zakzeski J, Bruijnincx PCA, Jongerius AL, Weckhuysen BM (2010) Chem Rev 110:3552

    Article  CAS  Google Scholar 

  10. Saito T, Brown RH, Hunt MA, Pickel DL, Pickel JM, Messman JM, Baker FS, Keller M, Naskar AK (2012) Green Chem 14:3295

    Article  CAS  Google Scholar 

  11. Sergeev AG, Hartwig JF (2011) Science 332:439

    Article  CAS  Google Scholar 

  12. Wu A, Patrick BO, Chung E, James BR (2012) Dalton Trans 41:11093

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  14. Yang Q, Shi J, Lin L, Peng L, Zhuang J (2012) Bioresour Technol 123:49

    Article  CAS  Google Scholar 

  15. Shimizu S, Yokoyama T, Akiyama T, Matsumoto Y (2012) J Agric Food Chem 60:6471

    Article  CAS  Google Scholar 

  16. El-Zawawy WK, Ibrahim MM, Belgacem MN, Dufresne A (2011) Mater Chem Phys 131:348

    Article  CAS  Google Scholar 

  17. Kim YS, Chang H-M, Kadla JF (2008) Holzforschung 62:38

    CAS  Google Scholar 

  18. Del Río JC, Gutiérrez A, Martínez ÁT (2004) Rapid Commun Mass Spectrom 18:1181

    Article  Google Scholar 

  19. Ralph J (1996) J Nat Prod 59:341

    Article  CAS  Google Scholar 

  20. Del Río JC, Marques G, Rencoret J, Martínez ÁT, Gutiérrez A (2007) J Agric Food Chem 55:5461

    Article  Google Scholar 

  21. Lu F, Ralph J (2002) Chem Commun 1:90–91

  22. Lu F, Ralph J (1996) Holzforschung 50:360

    Article  CAS  Google Scholar 

  23. Zhang L, Gellerstedt G (2007) Magn Reson Chem 45:37

    Article  CAS  Google Scholar 

  24. Capanema EA, Balakshin MY, Kadla JF (2005) J Agric Food Chem 53:9639

    Article  CAS  Google Scholar 

  25. Qu C, Kishimoto T, Kishino M, Hamada M, Nakajima N (2011) J Agric Food Chem 59:5382

    Article  CAS  Google Scholar 

  26. Nimz HH, Lüdemann HD (1976) Holzforschung 30:33

    Article  CAS  Google Scholar 

  27. Sonoda T, Ona T, Yokoi H, Ishida Y, Ohtani H, Tsuge S (2001) Anal Chem 73:5429

    Article  CAS  Google Scholar 

  28. Obataya E, Shibutani S, Minato K (2007) J Wood Sci 53:408

    Article  CAS  Google Scholar 

  29. Mörck R, Kringstad Knut P (1985) Holzforschung 39:109.

  30. Pu Y, Ragauskas AJ (2005) Can J Chem 83:2132

    Article  CAS  Google Scholar 

  31. Pizzi A, Zhou X, Navarrete P, Segovia C, Mansouri HR, Placentia Pena MI, Pichelin F (2013) J Adhes Sci Technol 27:252.

  32. Hoeger IC, Filpponen I, Martin-Sampedro R, Johansson L-S, Österberg M, Laine J, Kelley S, Rojas OJ (2012) Biomacromolecules 13:3228

    Article  CAS  Google Scholar 

  33. Qian Y, Deng Y, Qiu X, Li H, Yang D (2014) Green Chem 16:2156

    Article  CAS  Google Scholar 

  34. Ghosh I, Jain RK, Glasser WG (1999) J Appl Polym Sci 74:448

    Article  CAS  Google Scholar 

  35. Fulmer GR, Miller AJM, Sherden NH, Gottlieb HE, Nudelman A, Stoltz BM, Bercaw JE, Goldberg KI (2010) Organometallics 29:2176

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  37. Cho DW, Parthasarathi R, Pimentel AS, Maestas GD, Park HJ, Yoon UC, Dunaway-Mariano D, Gnanakaran S, Langan P, Mariano PS (2010) J Org Chem 75:6549

    Article  CAS  Google Scholar 

  38. Huo W, Li W, Zhang M, Fan W, Chang H-M, Jameel H (2014) Catal Lett 144:1159

  39. Baird IR, Rettig SJ, James BR, Skov KA (1998) Can J Chem 76:1379

    Article  CAS  Google Scholar 

  40. James BR, Addison AW, Cairns M, Dolphin D, Farrell NP, Paulson DR, Walker S (1979) In: Tsutsui M (ed) Fundamental research in homogeneous catalysis, ch. 50. Springer, New York

  41. Chow BC, Cohen IA (1971) Bioinorg Chem 1:57

    Article  CAS  Google Scholar 

  42. Enoki A, Goldsby G, Gold M (1981) Arch Microbiol 129:141

    Article  CAS  Google Scholar 

  43. Lauzon JMP, James BR Unpublished results. A summary of the findings is available in Table S3 in the ESI

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Acknowledgments

We thank the NSERC Lignoworks Network for funding, Weyerhaeuser Co (Seattle, WA, USA) for supplying the acetylated lignin, and a reviewer for constructive comments.

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Authors and Affiliations

  1. Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada

    Adam Wu, Jean Michel Lauzon & Brian R. James

Authors
  1. Adam Wu
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  2. Jean Michel Lauzon
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  3. Brian R. James
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Corresponding author

Correspondence to Brian R. James.

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Wu, A., Lauzon, J.M. & James, B.R. Hydrogenolysis of a γ-Acetylated Lignin Model Compound with a Ruthenium–Xantphos Catalyst. Catal Lett 145, 511–518 (2015). https://doi.org/10.1007/s10562-014-1401-7

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  • DOI: https://doi.org/10.1007/s10562-014-1401-7

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