Knocking on Wood: Base Metal Complexes as Catalysts for Selective Oxidation of Lignin Models and Extracts

Accounts of Chemical Research

Volumn 48, Issue 7, 2015, Pages 2037-2048

  Hanson, Susan K ^a   Baker, R Tom ^b  

^a LOS ALAMOS NATIONAL LABORATORY   (United States)

^b UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

LIGNIN; ORGANOMETALLIC COMPOUND;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION;

CATALYSIS; LIGNIN; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION;

EID: 84937510401     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.5b00104     Document Type: Article

References (56)

1. Collinson, S. R.; Thielemans, W. The Catalytic Oxidation of Biomass to New Materials Focusing on Starch, Cellulose and Lignin Coord. Chem. Rev. 2010, 254, 1854-1870
2. Zakzeski, J.; Bruijnincx, P. C. A.; Jongerius, A. L.; Weckhuysen, B. M. The Catalytic Valorization of Lignin for the Production of Renewable Chemicals Chem. Rev. 2010, 110, 3552-3599
3. Linger, J. G.; Vardon, D. R.; Guarnieri, M. T.; Karp, E. M.; Hunsinger, G. B.; Franden, M. A.; Johnson, C. W.; Chupka, G.; Strathman, T. J.; Pienkos, P. T.; Beckham, G. T. Lignin Valorisation through Integrated Biological Funneling and Chemical Catalysis Proc. Nat. Acad. Sci. 2014, 111, 12013-12018
4. Rahimi, A.; Ulbrich, A.; Coon, J. J.; Stahl, S. S. Formic Acid-Induced Depolymerization of Oxidized Lignin to Aromatics Nature 2014, 515, 249-252
5. Lancefield, C. S.; Ojo, O. S.; Tran, F.; Westwood, N. J. Isolation of Functionalized Phenolic Monomers through Selective Oxidation and C-O Bond Cleavage of the β-O-4 Linkages in Lignin Angew. Chem., Int. Ed. 2015, 54, 258-262
6. Alder, E. Lignin Chemistry- Past, Present, and Future Wood Sci. Technol. 1977, 11, 169-218
7. Nimz, H. Beech Lignin- Proposal of a Constitutional Scheme Angew. Chem., Int. Ed. 1974, 13, 313-321
8. Rencoret, J.; Gutiérrez, A.; Nieto, L.; Jiménez-Barbero, J.; Faulds, C. B.; Kim, H.; Ralph, J.; Martínez, A. T.; del Río, J. C. Lignin Composition and Structure in Young versus Adult Eucalyptus globulus Plants Plant Physiol. 2011, 155, 667-682
9. Crestini, C.; Crucianelli, M.; Orlandi, M.; Saladino, R. Oxidative Strategies in Lignin Chemistry: A New Environmentally Friendly Approach for the Functionalization of Lignin and Lignocellulose Fibers Catal. Today 2010, 156, 8-22
10. Parsell, T.; Yohe, S.; Degenstein, J.; Jarrell, T.; Klein, I.; Gencer, E.; Hewetson, B.; Hurt, M.; Kim, J. I.; Choudhari, H.; Saha, B.; Meilan, R.; Mosier, N.; Ribeiro, F.; Delgass, W. N.; Chapple, C.; Kenttämaa, H. I.; Agrawal, R.; Abu-Omar, M. M. A Synergistic Biorefinery Based on Catalytic Conversion of Lignin Prior to Cellulose Starting from Lignocellulosic Biomass Green Chem. 2015, 17, 1492-1499
11. Song, Q.; Wang, F.; Cai, J.; Wang, Y.; Zhang, J.; Yu, W.; Xu, J. Lignin Depolymerization (LDP) in Alcohol Over Nickel-Based Catalysts via a Fragmentation-Hydrogenolysis Process Energy Environ. Sci. 2013, 6, 994-1007
12. Vardon, D. R.; Franden, M. A.; Johnson, C. W.; Karp, E. M.; Guarnieri, M. T.; Linger, J. G.; Salm, M. J.; Strathmann, T. J.; Beckham, G. T. Adipic Acid Production from Lignin Energy Environ. Sci. 2015, 8, 617-628
13. Cui, F.; Dolphin, D. Metallophthalocyanines as Possible Lignin Peroxidase Models Bioorg. Med. Chem. 1995, 3, 471-477
14. Cui, F.; Wijesekera, T.; Dolphin, D.; Farrell, R.; Skerker, P. Biomimetic Degradation of Lignin J. Biotechnol. 1993, 30, 15-26
15. Crestini, C.; Caponi, M. C.; Argyropoulos, D. S.; Saladino, R. Immobilized Methyltrioxo Rhenium (MTO)/H2O2 Systems for the Oxidation of Lignin and Lignin Model Compounds Bioorg. Med. Chem. 2006, 14, 5292-5302
16. Crestini, C.; Pro, P.; Neri, V.; Saladino, R. Methyltrioxorhenium: a New Catalyst for the Activation of Hydrogen Peroxide to the Oxidation of Lignin and Lignin Model Compounds Bioorg. Med. Chem. 2005, 13, 2569-2578
17. Zakzeski, J.; Jongerius, A. L.; Weckhuysen, B. M. Transition Metal Catalyzed Oxidation of Alcell Lignin, Soda Lignin, and Lignin Model Compounds in Ionic Liquids Green Chem. 2010, 12, 1225-1236
18. Bolzacchini, E.; Chiavetto, L. B.; Canevali, C.; Morazzoni, F.; Orlandi, M.; Rindone, B. Oxidation of Propenoidic Phenols Catalysed by N,N '-ethylenebis(salicylideneiminato)cobalt(II) [Cosalen]: Reactivity and Spectroscopic Studies J. Mol. Catal. A 1996, 112, 347-351
19. Drago, R. S.; Corden, B. B.; Barnes, C. W. Novel Cobalt(II)-Catalyzed Oxidative Cleavage of a Carbon-Carbon Double Bond J. Am. Chem. Soc. 1986, 108, 2453-2454
20. Zombeck, A.; Drago, R. S.; Corden, B. B.; Gaul, J. H. Activation of Molecular Oxygen. Mechanistic Studies of the Oxidation of Hindered Phenols with Cobalt-Dioxygen Complexes J. Am. Chem. Soc. 1981, 103, 7580-7585
21. Biannic, B.; Bozell, J. J.; Elder, T. Steric Effects in the Design of Co-Schiff Base Complexes for the Catalytic Oxidation of Lignin Models to para -Benzoquinones Green Chem. 2014, 16, 3635-3642
22. Canevali, C.; Orlandi, M.; Pardi, L.; Rindone, B.; Scotti, R.; Sipila, J.; Morazzoni, F. Oxidative Degradation of Monomeric and Dimeric Phenylpropanoids: Reactivity and Mechanistic Investigation J. Chem. Soc., Dalton Trans. 2002, 3007-3014
23. Biannic, B.; Bozell, J. J. Efficient Cobalt-Catalyzed Oxidative Conversion of Lignin Models to Benzoquinones Org. Lett. 2013, 15, 2730-2733
24. Bozell, J. J.; Hames, B. R.; Dimmel, D. R. Cobalt-Schiff Base Complex Catalyzed Oxidation of Para-Substituted Phenolics. Preparation of Benzoquinones J. Org. Chem. 1995, 60, 2398-2404
25. Kervinen, K.; Allmendinger, M.; Leskelä, M.; Repo, T.; Rieger, B. In situ ATR-IR Spectroscopy: a Powerful Tool to Elucidate the Catalytic Oxidation of Veratryl Alcohol in Aqueous Media Phys. Chem. Chem. Phys. 2003, 5, 4450-4454
26. Kervinen, K.; Korpi, H.; Gerbrand Mesu, J.; Soulimani, F.; Repo, T.; Rieger, B.; Leskelä, M.; Weckhuysen, B. M. Mechanistic Insights into the Oxidation of Veratryl Alcohol with Co(salen) and Oxygen in Aqueous Media: An In-situ Spectroscopic Study Eur. J. Inorg. Chem. 2005, 2005, 2591-2599
27. Bolzacchini, E.; Canevali, C.; Morazzoni, F.; Orlandi, M.; Rindone, B.; Scotti, R. Spectromagnetic Investigation of the Active Species in the Oxidation of Propenoidic Phenols Catalysed by [ N,N -bis(salicylidene)-ethane-1,2-diaminato]cobalt(II) J. Chem. Soc., Dalton Trans. 1997, 4695-4699
28. Lanfranchi, M.; Prati, L.; Rossi, M.; Tiripicchio, A. The Oxidation of Ethane-1,2-diol Resulting from Molecular Oxygen Activation by Copper: Formation of an Oxoethanoate Complex Precedes Carbon-carbon Bond Cleavage J. Chem. Soc., Chem. Commun. 1993, 1698-1699
29. Prati, L.; Rossi, M. Stepwise Oxidation of 1,2-Diols Resulting from Molecular Oxygen Activation by Copper J. Mol. Catal. A: Chem 1996, 110, 221-226
30. Hanson, S. K.; Baker, R. T.; Gordon, J. C.; Scott, B. L.; Sutton, A. D.; Thorn, D. L. Aerobic Oxidation of Pinacol by Vanadium(V) Dipicolinate Complexes: Evidence for Reduction to Vanadium(III) J. Am. Chem. Soc. 2009, 131, 428-429
31. Hanson, S. K.; Baker, R. T.; Gordon, J. C.; Scott, B. L.; Thorn, D. L. Aerobic Oxidation of Lignin Models Using a Base Metal Vanadium Catalyst Inorg. Chem. 2010, 49, 5611-5618
32. Jiang, N.; Ragauskas, A. J. Vanadium-Catalyzed Selective Aerobic Alcohol Oxidation in Ionic Liquid [bmim]PF6 Tetrahedron Lett. 2007, 48, 273-276
33. Hanson, S. K.; Wu, R.; Silks, L. A. Mild and Selective Vanadium-Catalyzed Oxidation of Benzylic, Allylic, and Propargylic Alcohols Org. Lett. 2011, 13, 1908-1911
34. Zhang, G.; Scott, B. L.; Wu, R.; Silks, L. A.; Hanson, S. K. Aerobic Oxidation Reactions Catalyzed by Vanadium Complexes of Bis(Phenolate) Ligands Inorg. Chem. 2012, 51, 7354-7361
35. Arends, I. W. C. E.; Gamez, P.; Sheldon, R. A. Green Oxidation of Alcohols Using Biomimetic Cu Complexes and Cu Enzymes as Catalysts Adv. Inorg. Chem. 2006, 58, 235-279
36. Markó, I. E.; Gautier, A.; Dumeunier, R.; Doda, K.; Philippart, F.; Brown, S. M.; Urch, C. J. Efficient, Copper-Catalyzed, Aerobic Oxidation of Primary Alcohols Angew. Chem., Int. Ed. 2004, 43, 1588-1591
37. Gamez, P.; Arends, I. W. C. E.; Sheldon, R. A.; Reedijk, J. Room Temperature Aerobic Copper-Catalysed Selective Oxidation of Primary Alcohols to Aldehydes Adv. Synth. Catal. 2004, 346, 805-811
38. Sheldon, R. A.; Arends, I. W. C. E. Catalytic Oxidations Mediated by Metal Ions and Nitroxyl Radicals J. Mol. Catal. A: Chem 2006, 251, 200-214
39. Sedai, B.; Díaz-Urrutia, C.; Baker, R. T.; Wu, R.; Silks, L. A.; Hanson, S. K. Comparison of Copper and Vanadium Homogeneous Catalysts for Aerobic Oxidation of Lignin Models ACS Catal. 2011, 1, 794-804
40. Hanson, S. K.; Baker, R. T.; Gordon, J. C.; Scott, B. L.; Silks, L. A.; Thorn, D. L. Mechanism of Alcohol Oxidation by Dipicolinate Vanadium(V): Unexpected Role of Pyridine J. Am. Chem. Soc. 2010, 132, 17804-17816
41. Roček, J.; Aylward, D. E. One-Electron vs. Two-Electron Oxidations. Vanadium(V) Oxidation of Cyclobutanols J. Am. Chem. Soc. 1975, 97, 5452-5456
42. Chen, C. T.; Kao, J. Q.; Salunke, S. B.; Lin, Y. H. Enantioselective Aerobic Oxidation of α-Hydroxy-Ketones Catalyzed by Oxidovanadium(V) Methoxides Bearing Chiral, N -Salicylidene- tert -butylglycinates Org. Lett. 2011, 13, 26-29
43. Wigington, B. N.; Drummond, M. L.; Cundari, T. R.; Thorn, D. L.; Hanson, S. K.; Scott, S. L. A Biomimetic Pathway for Vanadium-Catalyzed Aerobic Oxidation of Alcohols: Evidence for a Base-Assisted Dehydrogenation Mechanism Chem.-Eur. J. 2012, 18, 14981-14988
44. Hoover, J. M.; Ryland, B. L.; Stahl, S. S. Mechanism of Copper(I)/TEMPO-Catalyzed Aerobic Alcohol Oxidation J. Am. Chem. Soc. 2013, 135, 2357-2367
45. Ryland, B. L.; McCann, S. D.; Brunold, T. C.; Stahl, S. S. Mechanism of Alcohol Oxidation Mediated by Copper(II) and Nitroxyl Radicals J. Am. Chem. Soc. 2014, 136, 12166-12173
46. Demmin, T. R.; Swerdloff, M. D.; Rogić, M. M. Copper(II)-Induced Oxidations of Aromatic Substrates: Catalytic Conversion of Catechols to o-Benzoquinones. Copper Phenoxides as Intermediates in the Oxidation of Phenol and a Single-Step Conversion of Phenol, Ammonia, and Oxygen into Muconic Acid Mononitrile J. Am. Chem. Soc. 1981, 103, 5795-5804
47. Sun, H.; Li, X.; Sundermeyer, J. Aerobic Oxidation of Phenol to Quinone with Copper Chloride as Catalyst in Ionic Liquid J. Mol. Catal. A: Chem 2005, 240, 119-122
48. Chaudhuri, P.; Hess, M.; Müller, J.; Hildenbrand, K.; Bill, E.; Weyhermüller, T.; Wieghardt, K. Aerobic Oxidation of Primary Alcohols (Including Methanol) by Copper(II)- and Zinc(II)-Phenoxyl Radical Catalysts J. Am. Chem. Soc. 1999, 121, 9599-9610
49. Zueva, E.; Walton, P. H.; McGrady, J. E. Catalytic Alcohol Oxidation by an Unsymmetrical 5-Coordinate Copper Complex: Electronic Structure and Mechanism Dalton Trans. 2006, 159-167
50. Pardini, V. L.; Vargas, R. R.; Viertler, H.; Utley, J. H. P. Anodic Cleavage of Lignin Model Dimers in Methanol Tetrahedron 1992, 48, 7221-7228
51. Rahimi, A.; Azarpira, A.; Kim, H.; Ralph, J.; Stahl, S. S. Chemoselective Metal-Free Aerobic Alcohol Oxidation in Lignin J. Am. Chem. Soc. 2013, 135, 6415-6418
52. Son, S.; Toste, F. D. Non-Oxidative Vanadium-Catalyzed C-O Bond Cleavage: Application to Degradation of Lignin Model Compounds Angew. Chem., Int. Ed. 2010, 49, 3791-3794
53. Hanson, S. K.; Wu, R.; Silks, L. A. C-C or C-O Bond Cleavage in a Phenolic Lignin Model Compound: Selectivity Depends on Vanadium Catalyst Angew. Chem., Int. Ed. 2012, 51, 3410-3413
54. Sedai, B.; Díaz-Urrutia, C.; Baker, R. T.; Wu, R.; Silks, L. A.; Hanson, S. K. Aerobic Oxidation of β-1 Lignin Model Compounds with Copper and Oxovanadium Catalysts ACS Catal. 2013, 3, 3111-3122
55. Arato, C.; Pye, E. K.; Gjennestad, G. The Lignol Approach to Biorefining of Woody Biomass to Produce Ethanol and Chemicals Appl. Biochem. Biotechnol. 2005, 121-124, 871-882
56. Díaz-Urrutia, C.; Chen, W. C.; Crites, C. O.; Baker, R. T. Towards Lignin Valorization: Comparing Homogeneous Catalysts for the Aerobic Oxidation and Depolymerization of Organosolv Lignin. 2015, In submission.