Homogeneous catalysis for the production of low-volume, high-value chemicals from biomass

Nature Reviews Chemistry

Volumn 2, Issue 5, 2018, Pages 35-46

  Bender, Trandon A ^a   Dabrowski, Jennifer A ^b   Gagné, Michel R ^a  

^a University of North Carolina at Chapel Hill   (United States)

^b ELON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85053198897     PISSN: None     EISSN: 23973358     Source Type: Journal    
DOI: 10.1038/s41570-018-0005-y     Document Type: Review

References (103)

1. Bozell, J. J. & Petersen, G. R. Technology development for the production of biobased products from biorefinery carbohydrates-the US Department of Energy’s ‘Top 10’ revisited. Green Chem. 12, 539–554 (2010)
2. Werpy, T. & Peterson, G. Top Value Added Chemicals from Biomass. Volume I: Results of Screening for Potential Candidates from Sugars and Synthesis Gas (U.S. Department of Energy, 2004)
3. Deuss, P. J., Barta, K. & de Vries, J. G. Homogeneous catalysis for the conversion of biomass and biomass-derived platform chemicals. Catal. Sci. Technol. 4, 1174–1196 (2014)
4. Corma, A., Iborra, S. & Velty, A. Chemical routes for the transformation of biomass into chemicals. Chem. Rev. 107, 2411 (2007)
5. Gilkey, M. J. & Xu, B. Heterogeneous catalytic transfer hydrogenation as an effective pathway in biomass upgrading. ACS Catal. 6, 1420–1436 (2016)
6. Chatterjee, C., Pong, F. & Sen, A. Chemical conversion pathways for carbohydrates. Green Chem. 17, 40–71 (2015)
7. Robinson, A. M., Hensley, J. E. & Medlin, J. W. Bifunctional catalysts for upgrading of biomass-derived oxygenates: a review. ACS Catal. 6, 5026–5043 (2016)
8. Young, R. A. The chemistry of solid wood. Wood Sci. Technol. 19, 17–18 (1985)
9. Román-Leshkov, Y., Chheda, J. N. & Dumesic, J. A. Phase modifiers promote efficient production of hydroxymethylfurfural from fructose. Science 312, 1933–1937 (2006)
10. Tollefson, J. Not your father’s biofuels: if biofuels are to help the fight against climate change, they have to be made from more appropriate materials and in better ways. Jeff Tollefson asks what innovation can do to improve the outlook. Nature 451, 880–884 (2008)
11. Xiong, M., Schneiderman, D. K., Bates, F. S., Hillmyer, M. A. & Zhang, K. Scalable production of mechanically tunable block polymers from sugar. Proc. Natl Acad. Sci. USA 111, 8357–8362 (2014)
12. Chheda, J. N., Huber, G. W. & Dumesic, J. A. Liquid-phase catalytic processing of biomass-derived oxygenated hydrocarbons to fuels and chemicals. Angew. Chem. Int. Ed. 46, 7164–7183 (2007)
13. Huber, G. W., Chheda, J. N., Barrett, C. J. & Dumesic, J. A. Production of liquid alkanes by aqueous-phase processing of biomass-derived carbohydrates. Science 308, 1446–1450 (2005)
14. Kunkes, E. L. et al. Catalytic conversion of biomass to monofunctional hydrocarbons and targeted liquid-fuel classes. Science 322, 417–421 (2008)
15. Metzger, J. O. Production of liquid hydrocarbons from biomass. Angew. Chem. Int. Ed. 45, 696–698 (2006)
16. Adduci, L. L., McLaughlin, M. P., Bender, T. A., Becker, J. J. & Gagné, M. R. Metal-free deoxygenation of carbohydrates. Angew. Chem. Int. Ed. 53, 1646–1649 (2014)
17. McLaughlin, M. P., Adduci, L. L., Becker, J. J. & Gagne, M. R. Iridium-catalyzed hydrosilylative reduction of glucose to hexane(s). J. Am. Chem. Soc. 135, 1225 (2013)
18. Mahdi, T. & Stephan, D. W. Enabling catalytic ketone hydrogenation by frustrated Lewis pairs. J. Am. Chem. Soc. 136, 15809–15812 (2014)
19. Scott, D. J., Fuchter, M. J. & Ashley, A. E. Nonmetal catalyzed hydrogenation of carbonyl compounds. J. Am. Chem. Soc. 136, 15813–15816 (2014)
20. Kamm, B., Kamm, M., Gruber, P. R. & Kromus, S. in Biorefineries — Industrial Processes and Products: Status Quo and Future Directions 1–40 (Wiley-VCH, 2008)
21. van Putten, R.-J. et al. Hydroxymethylfurfural, a versatile platform chemical made from renewable resources. Chem. Rev. 113, 1499–1597 (2013)
22. Zakrzewska, M. E., Bogel-Łukasik, E. & Bogel-Łukasik, R. Ionic liquid-mediated formation of 5-hydroxymethylfurfural — a promising biomass-derived building block. Chem. Rev. 111, 397–417 (2011)
23. Ståhlberg, T., Fu, W., Woodley, J. M. & Riisager, A. Synthesis of 5-(hydroxymethyl)furfural in ionic liquids: paving the way to renewable chemicals. ChemSusChem 4, 451–458 (2011)
24. Rosatella, A. A., Simeonov, S. P., Frade, R. F. M. & Afonso, C. A. M. 5-Hydroxymethylfurfural (HMF) as a building block platform: biological properties, synthesis and synthetic applications. Green Chem. 13, 754–793 (2011)
25. 12 furoin and alkane fuel. ACS Catal. 4, 1302–1310 (2014)
26. Liu, D. & Chen, E. Y.-X. Diesel and alkane fuels from biomass by organocatalysis and metal–acid tandem catalysis. ChemSusChem 6, 2236–2239 (2013)
27. Mou, Z. & Chen, E. Y.-X. Polyesters and poly(ester-urethane)s from biobased difuranic polyols. ACS Sustain. Chem. Eng. 4, 7118–7129 (2016)
28. 3 . J. Am. Chem. Soc. 118, 9448–9449 (1996)
29. Dauth, A. & Love, J. A. Reactivity by design — metallaoxetanes as centerpieces in reaction development. Chem. Rev. 111, 2010–2047 (2011)
30. Ziegler, J. E., Zdilla, M. J., Evans, A. J. & Abu-Omar, M. M. H2-driven deoxygenation of epoxides and diols to alkenes catalyzed by methyltrioxorhenium. Inorg. Chem. 48, 9998–10000 (2009)
31. Vkuturi, S., Chapman, G., Ahmad, I. & Nicholas, K. M. Rhenium-catalyzed deoxydehydration of glycols by sulfite. Inorg. Chem. 49, 4744–4746 (2010)
32. Shiramizu, M. & Toste, F. D. Deoxygenation of biomass-derived feedstocks: oxorhenium-catalyzed deoxydehydration of sugars and sugar alcohols. Angew. Chem. Int. Ed. 51, 8082–8086 (2012)
33. Boucher-Jacobs, C. & Nicholas, K. M. in Selective Catalysis for Renewable Feedstocks and Chemicals (ed. Nicholas, K. M.) 163–184 (Springer International Publishing, 2014)
34. Furimsky, E. Catalytic hydrodeoxygenation. Appl. Catal. A Gen. 199, 147–190 (2000)
35. Mascal, M. & Nikitin, E. B. High-yield conversion of plant biomass into the key value-added feedstocks 5-(hydroxymethyl)furfural, levulinic acid, and levulinic esters via 5-(chloromethyl)furfural. Green Chem. 12, 370–373 (2010)
36. Mascal, M. & Nikitin, E. B. Direct, high-yield conversion of cellulose into biofuel. Angew. Chem. Int. Ed. 47, 7924–7926 (2008)
37. Drosos, N. & Morandi, B. Boron-catalyzed regioselective deoxygenation of terminal 1,2-diols to 2-alkanols enabled by the strategic formation of a cyclic siloxane intermediate. Angew. Chem. Int. Ed. 54, 8814–8818 (2015)
38. 3 /silane system. Synlett 27, 1760–1764 (2016)
39. 3 -catalyzed chemoselective defunctionalization of ether-containing primary alkyl tosylates with hydrosilanes. Angew. Chem. Int. Ed. 56, 3389–3391 (2017)
40. Yasuda, M., Onishi, Y., Ueba, M., Miyai, T. & Baba, A. Direct reduction of alcohols: highly chemoselective reducing system for secondary or tertiary alcohols using chlorodiphenylsilane with a catalytic amount of indium trichloride. J. Org. Chem. 66, 7741 (2001)
41. Adduci, L. L., Bender, T. A., Dabrowski, J. A. & Gagné, M. R. Chemoselective conversion of biologically sourced polyols into chiral synthons. Nat. Chem. 7, 576–581 (2015)
42. Kottke, R. H. in Kirk-Othmer Encyclopedia of Chemical Technology (ed. Seidel, A.) (John Wiley and Sons, 2000)
43. Ahmed Foskey, T. J., Heinekey, D. M. & Goldberg, K. I. Partial deoxygenation of 1,2-propanediol catalyzed by iridium pincer complexes. ACS Catal. 2, 1285–1289 (2012)
44. Brentzel, Z. J. et al. Chemicals from biomass: combining ring-opening tautomerization and hydrogenation reactions to produce 1,5-pentanediol from furfural. ChemSusChem 10, 1351–1355 (2017)
45. Wu, L., Moteki, T., Gokhale, A. A., Flaherty, D. W. & Toste, F. D. Production of fuels and chemicals from biomass: condensation reactions and beyond. Chem 1, 32–58 (2017)
46. Ghosh, A. K. & Brindisi, M. Achmatowicz reaction and its application in the syntheses of bioactive molecules. RSC Adv. 6, 111564–111598 (2016)
47. Li, Z. & Tong, R. Catalytic environmentally friendly protocol for Achmatowic rearrangement. J. Org. Chem. 81, 4847–4855 (2016)
48. Takeuchi, M., Taniguchi, T. & Ogasawara, K. Back to the Sugars: a new enantio and diastereocontrolled route to hexoses from furfural. Synthesis 1999, 341–354 (1999)
49. Fürstner, A. & Nagano, T. Total syntheses of ipomoeassin B and E. J. Am. Chem. Soc. 129, 1906–1907 (2007)
50. Jackson, K. L., Henderson, J. A., Morris, J. C., Motoyoshi, H. & Phillips, A. J. A synthesis of the C1–C15 domain of the halichondrins. Tetrahedron Lett. 49, 2939–2941 (2008)
51. Nagano, T. et al. Total synthesis and biological evaluation of the cytotoxic resin glycosides ipomoeassin A–F and analogues. Chem. Eur. J. 15, 9697–9706 (2009)
52. Prasad, K. R. & Pawar, A. B. Enantioselective formal synthesis of palmerolide A. Org. Lett. 13, 4252–4255 (2011)
53. Prasad, K. R. & Revu, O. Total synthesis of (+)-seimatopolide A. J. Org. Chem. 79, 1461–1466 (2014)
54. Ashmus, R. A., Jayasuriya, A. B., Lim, Y.-J., O’Doherty, G. A. & Lowary, T. L. De novo asymmetric synthesis of a 6-O-Methyl-d-glycero-l-gluco-heptopyranose-derived thioglycoside for the preparation of Campylobacter jejuni NCTC11168 capsular polysaccharide fragments. J. Org. Chem. 81, 3058–3063 (2016)
55. Monrad, R. N. & Madsen, R. Rhodium-catalyzed decarbonylation of aldoses. J. Org. Chem. 72, 9782–9785 (2007)
56. + . Organometallics 29, 1045 (2010)
57. Liguori, F., Moreno-Marrodan, C. & Barbaro, P. Environmentally friendly synthesis of β-valerolactone by direct catalytic conversion of renewable sources. ACS Catal. 5, 1882–1894 (2015)
58. Goulas, K. A. & Toste, F. D. Combining microbial production with chemical upgrading. Curr. Opin. Biotechnol. 38, 47–53 (2016)
59. Cabrele, C. & Reiser, O. The modern face of synthetic heterocyclic chemistry. J. Org. Chem. 81, 10109–10125 (2016)
60. Marson, C. M. New and unusual scaffolds in medicinal chemistry. Chem. Soc. Rev. 40, 5514–5533 (2011)
61. Llevot, A. et al. Renewability is not enough: recent advances in the sustainable synthesis of biomass-derived monomers and polymers. Chem. Eur. J. 22, 11510–11521 (2016)
62. Foster, R. W., Tame, C. J., Bucar, D.-K., Hailes, H. C. & Sheppard, T. D. Sustainable synthesis of chiral tetrahydrofurans through the selective dehydration of pentoses. Chem. Eur. J. 21, 15947–15950 (2015)
63. Koh, P.-F., Wang, P., Huang, J.-M. & Loh, T.-P. Biomass derived furfural-based facile synthesis of protected (2S)-phenyl-3-piperidone, a common intermediate for many drugs. Chem. Commun. 50, 8324–8327 (2014)
64. Veits, G. K., Wenz, D. R. & Read de Alaniz, J. Versatile method for the synthesis of 4-aminocyclopentenones: dysprosium(III) triflate catalyzed aza-piancatelli rearrangement. Angew. Chem. Int. Ed. 49, 9484–9487 (2010)
65. Bloom, P. D. & Venkitasubramanian, P. Monomers and polymers from bioderived carbon. US Patent US20090018300A1 (2008)
66. Hammond, W., East, A., Jaffe, M. & Feng, X. Isosorbide-derived epoxy resins and methods of making same. US Patent US20150307650A1 (2015)
67. Tachdjian, C., Karanewsky, D. S., Adamski-Werner, S. L., Yamamoto, J. M. & Servant, G. Isosorbide derivatives and their use as flavor modifiers, tastants, and taste enhancers. US Patent US20130295261A1 (2013)
68. Bähn, S. et al. The catalytic amination of alcohols. ChemCatChem 3, 1853–1864 (2011)
69. Yang, Q., Wang, Q. & Yu, Z. Substitution of alcohols by N-nucleophiles via transition metal-catalyzed dehydrogenation. Chem. Soc. Rev. 44, 2305–2329 (2015)
70. Pera-Titus, M. & Shi, F. Catalytic amination of biomass-based alcohols. ChemSusChem 7, 720–722 (2014)
71. Fink, J. K. in High Performance Polymers (ed. Fink, J. K.) 449–474 (William Andrew Publishing, 2008)
72. Young, I. S. & Baran, P. S. Protecting-group-free synthesis as an opportunity for invention. Nat. Chem. 1, 193–205 (2009)
73. Baran, P. S., Maimone, T. J. & Richter, J. M. Total synthesis of marine natural products without using protecting groups. Nature 446, 404–408 (2007)
74. Wei, X.-F., Shimizu, Y. & Kanai, M. An expeditious synthesis of sialic acid derivatives by copper(I)-catalyzed stereodivergent propargylation of unprotected aldoses. ACS Cent. Sci. 2, 21–26 (2016)
75. Richter, C., Krumrey, M., Bahri, M., Trunschke, S. & Mahrwald, R. Amine-catalyzed cascade reactions of unprotected aldoses — an operationally simple access to defined configured stereotetrads or stereopentads. ACS Catal. 6, 5549–5552 (2016)
76. 2 O−NaI Lewis acid promoter: investigation into the Garcia Gonzalez reaction in solvent-free conditions. J. Org. Chem. 72, 6029–6036 (2007)
77. Calter, M. A., Zhu, C. & Lachicotte, R. J. Rapid synthesis of the 7-deoxy zaragozic acid core. Org. Lett. 4, 209–212 (2002)
78. Paterson, I., Feßner, K., Finlay, M. R. V. & Jacobs, M. F. Studies towards the synthesis of the zaragozic acids: a novel epoxide cyclisation approach to the formation of the bicyclic acetal core. Tetrahedron Lett. 37, 8803–8806 (1996)
79. Liu, J.-H. & Long, Y.-Q. Studies toward the total synthesis of cyclodidemniserinol trisulfate. Part II: 3,5,7-Trisubstituted 6,8-dioxabicyclo [3.2.1] octane core structure construction via I2-mediated deprotection and ring closure tandem reaction. Tetrahedron Lett. 50, 4592–4594 (2009)
80. Shing, T. K. M. & Cheng, H. M. Intramolecular direct aldol reactions of sugar 2,7-diketones: syntheses of hydroxylated cycloalka(e)nones. Org. Biomol. Chem. 13, 4795–4802 (2015)
81. Bauer, J. & Osborn, H. M. I. Sialic acids in biological and therapeutic processes: opportunities and challenges. Future Med. Chem. 7, 2285–2299 (2015)
82. 3 -catalyzed reductive carbocyclization of unsaturated carbohydrates. Org. Lett. 18, 4120–4123 (2016)
83. Hazra, C. K., Gandhamsetty, N., Park, S. & Chang, S. Borane catalysed ring opening and closing cascades of furans leading to silicon functionalized synthetic intermediates. Nat. Commun. 7, 13431 (2016)
84. Wong, H. N. C. et al. Use of cyclopropanes and their derivatives in organic synthesis. Chem. Rev. 89, 165–198 (1989)
85. Böhm, C. et al. A new strategy for the stereoselective synthesis of 1,2,3-trisubstituted cyclopropanes. Eur. J. Org. Chem. 2000, 2955–2965 (2000)
86. Kalidindi, S. et al. Enantioselective synthesis of arglabin. Angew. Chem. Int. Ed. 46, 6361–6363 (2007)
87. Mix, K. A., Aronoff, M. R. & Raines, R. T. Diazo compounds: versatile tools for chemical biology. ACS Chem. Biol. 11, 3233–3244 (2016)
88. Li, W., Niu, Y., Xiong, D.-C., Cao, X. & Ye, X.-S. Highly substituted cyclopentane–CMP conjugates as potent sialyltransferase inhibitors. J. Med. Chem. 58, 7972–7990 (2015)
89. Quintard, A., Lefranc, A. & Alexakis, A. Highly enantioselective direct vinylogous michael addition of γ-butenolide to enals. Org. Lett. 13, 1540–1543 (2011)
90. Wu, B., Yu, Z., Gao, X., Lan, Y. & Zhou, Y.-G. Regioselective α-addition of deconjugated butenolides: enantioselective synthesis of dihydrocoumarins. Angew. Chem. Int. Ed. 56, 4006–4010 (2017)
91. Mäki-Arvela, P., Simakova, I. L., Salmi, T. & Murzin, D. Y. Production of lactic acid/lactates from biomass and their catalytic transformations to commodities. Chem. Rev. 114, 1909–1971 (2014)
92. Chen, K., Li, X., Zhang, S.-Q. & Shi, B.-F. Synthesis of chiral α-hydroxy acids via palladium-catalyzed C(sp3)-H alkylation of lactic acid. Chem. Commun. 52, 1915–1918 (2016)
93. Ansari, A. A., Lahiri, R. & Vankar, Y. D. The carbon-Ferrier rearrangement: an approach towards the synthesis of C -glycosides. Arkivoc, 316–362 (2013)
94. Dechert-Schmitt, A.-M. R., Schmitt, D. C. & Krische, M. J. Protecting-group-free diastereoselective C–C coupling of 1,3-glycols and allyl acetate through site-selective primary alcohol dehydrogenation. Angew. Chem. Int. Ed. 52, 3195–3198 (2013)
95. Ulbrich, K., Kreitmeier, P. & Reiser, O. Microwave- or microreactor-assisted conversion of furfuryl alcohols into 4-hydroxy-2-cyclopentenones. Synlett 2010, 2037–2040 (2010)
96. Dobler, D. & Reiser, O. Synthesis of 6-substituted 2-pyrones starting from renewable resources: total synthesis of sibirinone, (e)-6-(pent-1-en-1-yl)-2h-pyran-2-one, and (e)-6-(hept-1-en-1-yl)-2h-pyran-2-one. J. Org. Chem. 81, 10357–10365 (2016)
97. Zheng, X.-Y. et al. Selective formation of chromogen I from N-acetyl-D-glucosamine upon lanthanide coordination. Inorg. Chem. 56, 110–113 (2017)
98. Brovetto, M., Gamenara, D., Saenz Méndez, P. & Seoane, G. A. C−C bond-forming lyases in organic synthesis. Chem. Rev. 111, 4346–4403 (2011)
99. Nestl, B. M., Hammer, S. C., Nebel, B. A. & Hauer, B. New generation of biocatalysts for organic synthesis. Angew. Chem. Int. Ed. 53, 3070–3095 (2014)
100. Matsubara, K. et al. One-step synthesis of 2-keto-3-deoxy-d-gluconate by biocatalytic dehydration of d-gluconate. J. Biotechnol. 191, 69–77 (2014)
101. Van de Vyver, S., Odermatt, C., Romero, K., Prasomsri, T. & Román-Leshkov, Y. Solid Lewis acids catalyze the carbon–carbon coupling between carbohydrates and formaldehyde. ACS Catal. 5, 972–977 (2015)
102. Wheeldon, I., Christopher, P. & Blanch, H. Integration of heterogeneous and biochemical catalysis for production of fuels and chemicals from biomass. Curr. Opin. Biotechnol. 45, 127–135 (2017)
103. Luo, H. Y., Consoli, D. F., Gunther, W. R. & Román-Leshkov, Y. Investigation of the reaction kinetics of isolated Lewis acid sites in Beta zeolites for the Meerwein–Ponndorf–Verley reduction of methyl levulinate to γ-valerolactone. J. Catal. 320, 198–207 (2014)