Eco-friendly synthesis of 5-hydroxymethylfurfural (HMF) and its application to the Ferrier-rearrangement reaction

References

• Dou, Y.; Zhou, S.; Oldani, C.; Fang, W.; Cao, Q. 5-Hydroxymethylfurfural production from dehydration of fructose catalyzed by Aquivion@silica solid acid. Fuel 2018, 214, 45–54. 10.1016/j.fuel.2017.10.124.
   Web of Science ®Google Scholar
• Xia, H.; Xu, S.; Yang, L. Efficient conversion of wheat straw into furan compounds, bio-oils, and phosphate fertilizers by a combination of hydrolysis and catalytic pyrolysis. RSC Adv. 2017, 7 (3), 1200–1205. 10.1039/C6RA27072G.
   Web of Science ®Google Scholar
• Du, X.; Zhang, J.; Wang, Y.; Qu, Y. Conversion of carbohydrates into platform chemicals catalyzed by alkaline ionic liquids. Catalysts 2017, 7 (9), 245. 10.3390/catal7090245.
   Web of Science ®Google Scholar
• Yutthalekha, T.; Suttipat, D.; Salakhum, S.; Thivasasith, A.; Nokbin, S.; Limtrakul, J.; Wattanakit, C. Aldol condensation of biomass-derived platform molecules over amine-grafted hierarchical FAU-type zeolite nanosheets (Zeolean) featuring basic sites. Chem. Commun., 2017, 53, 12185–12188. 10.1039/c7cc06375j.
   PubMed Web of Science ®Google Scholar
• Kucherov, F. A.; Gordeev, E. G.; Kashin, A. S.; Ananikov, V. P., Three-dimensional printing with biomass-derived PEF for carbon-neutral manufacturing. Angew. Chem. Int. Ed. 2017, 56, 1–6.
   Web of Science ®Google Scholar
• Qiu, G.; Wang, X.; Huang, C.; Li, Y.; Chen, B. Facile, One-Pot Two-step, strategy for the production of potential bio-diesel candidates from fructose. Catalysts 2017, 7 (8), 237. 10.3390/catal7080237.
   Web of Science ®Google Scholar
• Xia, H.; Houghton, J. A.; Clark, J. H.; Matharu, A. S. Potential utilization of unavoidable food supply chain wastes – Valorization of pea vine wastes. ACS Sustain. Chem. Eng. 2016, 4 (11), 6002–6009. 10.1021/acssuschemeng.6b01297.
   Web of Science ®Google Scholar
• Wang, Z.; Chen, Q. Conversion of 5-hydroxymethylfurfural into 5-ethoxymethylfurfural and ethyl levulinate catalyzed by MOF-based heteropolyacid materials. Green Chem. 2016, 18, 5884–5889. 10.1039/C6GC01206J.
   Web of Science ®Google Scholar
• Wang, Y.; Yu, K.; Lei, D.; Si, W.; Feng, Y.; Lou, L.-L.; Liu, S. Basicity-tuned hydrotalcite-supported Pd catalysts for aerobic oxidation of 5-hydroxymethyl-2-furfural under mild conditions. ACS Sustain. Chem. Eng. 2016, 4 (9), 4752–4761. 10.1021/acssuschemeng.6b00965.
   Web of Science ®Google Scholar
• Song, Y.; Wang, X.; Qu, Y.; Huang, C.; Li, Y.; Chen, B. Efficient dehydration of fructose to 5-hydroxy-methylfurfural catalyzed by heteropolyacid salts. Catalysts 2016, 6 (4), 49. 10.3390/catal6040049.
   Web of Science ®Google Scholar
• Roman-Leshkov, Y.; Chheda, J. N.; Dumesic, J. A. Phase modifiers promote efficient production of hydroxymethylfurfural from fructose. Science 2006, 312, 1933–1937. 10.1126/science.1126337.
   PubMed Web of Science ®Google Scholar
• Shen, Y.; Zhang, Y.; Zhu, E.; Chen, Y.; Jin, P.; Liu, M.; Yan, Y.; Li, C. Facile synthesis of hierarchical pore foam catalysts with Brønsted–Lewis acid sites for the one-pot conversion of cellulose to 5-hydroxymethylfurfural. RSC Adv. 2016, 6 (84), 80368–80382. 10.1039/C6RA14615E.
   Web of Science ®Google Scholar
• 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. 2011, 13 (4), 754. 10.1039/c0gc00401d.
   Web of Science ®Google Scholar
• Roman-Leshkov, Y.; Barrett, C. J.; Liu, Z. Y.; Dumesic, J. A. Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates. Nature 2007, 447 (7147), 982–5. 10.1038/nature05923.
   PubMed Web of Science ®Google Scholar
• Ly, N.; Al-Shamery, K.; Chan-Thaw, C. E.; Prati, L.; Carniti, P.; Gervasini, A. Impact of support oxide acidity in Pt-catalyzed HMF hydrogenation in alcoholic medium. Catal. Lett. 2016, 147, 345–359. 10.1007/s10562-016-1945-9.
   Web of Science ®Google Scholar
• Pacheco, J. J.; Davis, M. E. Synthesis of terephthalic acid via Diels–Alder reactions with ethylene and oxidized variants of 5-hydroxymethylfurfural. Proc. Natl. Acad. Sci. USA 2014, 111 (23), 8363–8367. 10.1073/pnas.1408345111.
   PubMed Web of Science ®Google Scholar
• Moshapo, P. T.; Sokamisa, M.; Mmutlane, E. M.; Mampa, R. M.; Kinfe, H. H. A convenient domino Ferrier rearrangement-intramolecular cyclization for the synthesis of novel benzopyran-fused pyranoquinolines. Org. Biomol. Chem. 2016, 14 (24), 5627–5638. 10.1039/C5OB02536B.
   PubMed Web of Science ®Google Scholar
• Dantas, C. R.; de Freitas, J. J.; Barbosa, Q. P.; Militao, G. C.; Silva, T. D.; da Silva, T. G.; Paulino, A. A.; Freitas, J. C.; Oliveira, R. A.; Menezes, P. H. Stereoselective synthesis and antitumoral activity of Z-enyne pseudoglycosides. Org. Biomol. Chem. 2016, 14 (28), 6786–6794. 10.1039/C6OB00945J.
   PubMed Web of Science ®Google Scholar
• Minbiole, E. C.; Minbiole, K. P. The Petasis-Ferrier rearrangement: developments and applications. J. Antibiot. (Tokyo) 2016, 69 (4), 213–219. 10.1038/ja.2015.136.
   PubMed Web of Science ®Google Scholar
• Zhou, J.; Chen, H.; Shan, J.; Li, J.; Yang, G.; Chen, X.; Xin, K.; Zhang, J.; Tang, J. FeCl3·6H2O/C: an efficient and recyclable catalyst for the synthesis of 2,3-unsaturated O- and S-glycosides. J. Carbohydr. Chem. 2014, 33 (6), 313–325. 10.1080/07328303.2014.941995.
   Web of Science ®Google Scholar
• Peh, G.; Floreancig, P. E. Convergent one-pot oxidative [n + 1] approaches to spiroacetal synthesis. Org. Lett. 2015, 17 (15), 3750–3753. 10.1021/acs.orglett.5b01736.
   PubMed Web of Science ®Google Scholar
• Rusin, A.; Zawisza-Puchalka, J.; Kujawa, K.; Gogler-Piglowska, A.; Wietrzyk, J.; Switalska, M.; Glowala-Kosinska, M.; Gruca, A.; Szeja, W.; Krawczyk, Z.; Grynkiewicz, G. Synthetic conjugates of genistein affecting proliferation and mitosis of cancer cells. Bioorg. Med. Chem. 2011, 19 (1), 295–305. 10.1016/j.bmc.2010.11.024.
   PubMed Web of Science ®Google Scholar
• Sun, G. S.; Qiu, S. F.; Ding, Z. K.; Chen, H. S.; Zhou, J. F.; Wang, Z. F.; Zhang, J. B. Magnetic core-shell Fe3O4@C-SO3H as an efficient and renewable ‘Green Catalyst’ for the synthesis of O-2,3-unsaturated glycopyranosides. Synlett 2017, 28 (3), 347–352.
   Web of Science ®Google Scholar
• Chen, H.; Luo, X.; Qiu, S.; Sun, W.; Zhang, J. TMSOTf mediated stereoselective synthesis of alpha-C-glycosides from unactivated aryl acetylenes. Glycoconj. J. 2017, 34 (1), 13–20. 10.1007/s10719-016-9718-7.
   PubMed Web of Science ®Google Scholar
• Zhang, J.; Zhang, B.; Zhou, J.; Chen, H.; Li, J.; Yang, G.; Wang, Z.; Tang, J. A facile H2SO4-SiO2–catalyzed Ferrier rearrangement of 3,4,6-tri-O-benzyl-d-glucal. J. Carbohydr. Chem. 2013, 32 (5–6), 380–391. 10.1080/07328303.2013.809093.
   Web of Science ®Google Scholar
• Zhou, J.; Zhang, B.; Yang, G.; Chen, X.; Wang, Q.; Wang, Z.; Zhang, J.; Tang, J. A facile H2SO4/4 Å molecular sieves catalyzed synthesis of 2,3-unsaturated O-glycosides via Ferrier-type rearrangement. Synlett 2010, 2010 (06), 893–896. 10.1055/s-0029-1219539.
   Google Scholar
• Zhou, J. F.; Chen, X.; Wang, Q. B.; Zhang, B.; Zhang, L. Y.; Yusulf, A.; Wang, Z. F.; Zhang, J. B.; Tang, J. H2SO4-SiO2: Highly efficient and novel catalyst for the Ferrier-type glycosylation. Chin. Chem. Lett. 2010, 21 (8), 922–926. 10.1016/j.cclet.2010.03.013.
   Web of Science ®Google Scholar
• Girka, Q.; Estrine, B.; Hoffmann, N.; Le Bras, J.; Marinković, S.; Muzart, J. Simple efficient one-pot synthesis of 5-hydroxymethylfurfural and 2,5-diformylfuran from carbohydrates. React. Chem. Eng. 2016, 1 (2), 176–182. 10.1039/C5RE00004A.
   Web of Science ®Google Scholar
• Kanzler, C.; Schestkowa, H.; Haase, P. T.; Kroh, L. W. Formation of reactive intermediates, color, and antioxidant activity in the maillard reaction of maltose in comparison to d-glucose. J. Agric. Food Chem. 2017, 65 (40), 8957–8965. 10.1021/acs.jafc.7b04105.
   PubMed Web of Science ®Google Scholar
• Tucker, M. H.; Alamillo, R.; Crisci, A. J.; Gonzalez, G. M.; Scott, S. L.; Dumesic, J. A. Sustainable solvent systems for use in tandem carbohydrate dehydration hydrogenation. ACS Sustain. Chem. Eng. 2013, 1 (5), 554–560. 10.1021/sc400044d.
   Web of Science ®Google Scholar
• Crisci, A. J.; Tucker, M. H.; Lee, M.-Y.; Jang, S. G.; Dumesic, J. A.; Scott, S. L. Acid-functionalized SBA-15-type silica catalysts for carbohydrate dehydration. ACS Catal. 2011, 1 (7), 719–728. 10.1021/cs2001237.
   Web of Science ®Google Scholar
• Xin, H.; Zhang, T.; Li, W.; Su, M.; Li, S.; Shao, Q.; Ma, L., Dehydration of glucose to 5-hydroxymethylfurfural and 5-ethoxymethylfurfural by combining Lewis and Brønsted acid. RSC Adv. 2017, 7 (66), 41546–41551. 10.1039/C7RA07684C.
   Web of Science ®Google Scholar
• Li, H.; Xu, W.; Huang, T.; Jia, S.; Xu, Z.; Yan, P.; Liu, X.; Zhang, Z. C. Distinctive aldose isomerization characteristics and the coordination chemistry of metal chlorides in 1-Butyl-3-methylimidazolium chloride. ACS Catal. 2014, 4 (12), 4446–4454. 10.1021/cs5012684.
   Web of Science ®Google Scholar
• Sau, A.; Williams, R.; Palo-Nieto, C.; Franconetti, A.; Medina, S.; Galan, M. C. Palladium-catalyzed direct stereoselective synthesis of deoxyglycosides from glycals. Angew. Chem. Int. Ed. 2017, 56 (13), 3640–3644. 10.1002/anie.201612071.
   PubMed Web of Science ®Google Scholar
• Chen, P.; Bi, B. Preparation of 2,3-unsaturated pseudoglycosides with Ferrier rearrangement promoted by Tm(OTf)3 as a highly efficient catalyst. Tetrahedron Lett. 2015, 56 (34), 4895–4899. 10.1016/j.tetlet.2015.06.077.
   Web of Science ®Google Scholar
• Chen, P.; Li, S. Y(OTf)3 as a highly efficient catalyst in Ferrier rearrangement for the synthesis of O- and S-2,3-unsaturated glycopyranosides. Tetrahedron Lett. 2014, 55 (42), 5813–5816. 10.1016/j.tetlet.2014.08.092.
   Web of Science ®Google Scholar
• Bound, D. J.; Bettadaiah, B. K.; Srinivas, P. ZnBr2-catalyzed and microwave-assisted synthesis of 2,3-unsaturated glucosides of hindered phenols and alcohols. Synth. Commun. 2014, 44 (17), 2565–2576. 10.1080/00397911.2014.909490.
   Web of Science ®Google Scholar
• Roy, R.; Rajasekaran, P.; Mallick, A.; Vankar, Y. D. Gold(III) chloride and phenylacetylene: A catalyst system for the Ferrier rearrangement, and O-glycosylation of 1-O-acetyl sugars as glycosyl donors. Eur. J. Org. Chem. 2014, 2014 (25), 5564–5573. 10.1002/ejoc.201402606.
   Web of Science ®Google Scholar
• Gómez, A. M.; Lobo, F.; Uriel, C.; López, J. C. Recent developments in the Ferrier rearrangement. Eur. J. Org. Chem. 2013, 2013 (32), 7221–7262. 10.1002/ejoc.201300798.
   Web of Science ®Google Scholar
• Tatina, M.; Kusunuru, A. K.; Yousuf, S. K.; Mukherjee, D. Tandem regio- and diastereo-selective synthesis of halogenated C-vinyl glycosides from unactivated arylacetylenes. Chem. Commun. 2013, 49 (97), 11409–11411. 10.1039/c3cc46914j.
   PubMed Web of Science ®Google Scholar
• Freitas, J. C. R.; Couto, T. R.; Paulino, A. A. S.; de Freitas Filho, J. R.; Malvestiti, I.; Oliveira, R. A.; Menezes, P. H. Stereoselective synthesis of pseudoglycosides catalyzed by TeCl4 under mild conditions. Tetrahedron 2012, 68 (51), 10611–10620. 10.1016/j.tet.2012.09.073.
   Web of Science ®Google Scholar
• Williams, D. B.; Simelane, S. B.; Kinfe, H. H. Aluminium triflate catalysed O-glycosidation: Temperature-switched selective Ferrier rearrangement or direct addition with alcohols. Org. Biomol. Chem. 2012, 10 (29), 5636–5642. 10.1039/c2ob25540e.
   PubMed Web of Science ®Google Scholar
• Qiu, S.; Sun, G.; Ding, Z.; Chen, H.; Zhang, J. Ferric chloride: An eco-friendly catalyst for the stereoselective synthesis of 2-deoxy aryl-O-rhamnosides. Synlett 2017, 28, 2024–2029. 10.1055/s-0036-1588864.
   Web of Science ®Google Scholar
• Qiu, S.; Zhang, W.; Sun, G.; Wang, Z.; Zhang, J. A facile and direct glycosidation method for the synthesis of 2-deoxy α-rhamnosides catalyzed by ferric chloride. ChemistrySelect 2016, 1 (15), 4840–4844. 10.1002/slct.201600802.
   Web of Science ®Google Scholar
• Yaya, S.; Sorhoa, S.; Cottier, L.; Descotes, G. Synthesis of 2,3-unsaturated furanic hex- and pent-enopyranoside employing the Ferrier rearrangement. Bull. Chem. Soc. Ethiopia 2005, 19 (2), 233–241.
   Web of Science ®Google Scholar
• Cottier, L. Synthesis of acetylated ranunculin diastereoisomers and δ-gluccsyl-γ-oxy-Oxo esters from α or β glucosy I methyIfurfura I. J. Carbohydr. Chem. 2005, 24, 55–71. 10.1081/CAR-200049688.
   Web of Science ®Google Scholar
• Filho, J. R. d. F.; Srivastava, R. M.; Soro, Y.; Cottier, L.; Descotes, G. Synthesis of new 2,3-unsaturated O-glycosides through Ferrier rearrangement. J. Carbohydr. Chem. 2001, 20, 561–567. 10.1081/CAR-100108274.
   Web of Science ®Google Scholar
• Lichtenthaler, F. W.; Martins, D.; Webera, T.; Schiweckb, H. 5-(a-D-Glucosyloxymethyl)furfural: Preparation from isomaltulose and exploration of its ensuing chemistry. Liebigs Ann. Chem. 1993, 967–974. 10.1002/jlac.1993199301154.
   Google Scholar
• Chen, H.; Xian, T.; Zhang, W.; Si, W.; Luo, X.; Zhang, B.; Zhang, M.; Wang, Z.; Zhang, J. An efficient method for the synthesis of pyranoid glycals. Carbohydr. Res. 2016, 431, 42–46. 10.1016/j.carres.2016.05.013.
   PubMed Web of Science ®Google Scholar
• Xu, G. G.; Pagare, P. P.; Ghatge, M. S.; Safo, R. P.; Gazi, A.; Chen, Q.; Safo, M. K.; Abdulmalik, O. Design, synthesis, and biological evaluation of ester and ether derivatives of antisickling agent 5-HMF for the treatment of sickle cell disease. Mol. Pharm. 2017, 14, 3499–3511. 10.1021/acs.molpharmaceut.7b00553.
   PubMed Web of Science ®Google Scholar
• Feng Z.; Zhan, Z.; Yang, Y.; Jiang, J.; Zhang, P. New heterocyclic compounds from Ranunculus ternatus Thunb. Bioorg. Chem. 2017, 74, 10–14. 10.1016/j.bioorg.2017.07.004.
   PubMed Web of Science ®Google Scholar
• Kuroda, M.; Mimaki, Y.; Sashida, Y.; Hirano, T.; Oka, K.; Dobashi, A.; Li, H.; Harada, N. Novel cholestane glycosides from the bulbs of Ornithogalum saundersiae and their cytostatic activity on leukemia HL-60 and MOLT-4 cells. Tetrahedron 1997, 53, 11549–11562. 10.1016/S0040-4020(97)00750-3.
   Web of Science ®Google Scholar