HFIP-assisted Brønsted acid catalysed synthesis of furan derivatives
Bonnie Pu A and Thanh Vinh Nguyen
A *
+ Author Affiliations
- Author Affiliations
A School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia.
Australian Journal of Chemistry 76(1) 58-62 https://doi.org/10.1071/CH22212
Submitted: 28 September 2022 Accepted: 16 November 2022 Published: 18 January 2023
© 2023 The Author(s) (or their employer(s)). Published by CSIRO Publishing. This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND)
Abstract
The furan framework is ubiquitous in naturally occurring compounds, and furan-containing structures are also key intermediates to many industrially important chemicals and materials. There have been reports of numerous methods to synthesise furans, however most of them use transition metal catalysts or Brønsted acid catalysts under harsh conditions. This work describes the development of a new non-metal Brønsted acid catalytic method for the synthesis of 2-aryl-3-carboxylate ester furans and 2,3-diaryl furans from ynone substrates. The method was shown to be efficient under very mild reaction conditions with up to 94% product yields.
Keywords: Brønsted acid catalysis, catalysis, cyclization reaction, furan, HFIP, hydrogen‐bonding, metal‐free, solvent effect.
References
[1] Kwiecień H, Wodnicka A. 5.3 - Five-Membered Ring Systems: Furans and Benzofurans. In Gribble GW, Joule JA, editors. Progress in Heterocyclic Chemistry. Vol. 31. Elsevier; 2020. pp. 281–323.[2] FN Peters Jr, Industrial Uses of Furans. Ind Eng Chem 1939, 31, 178.
| Industrial Uses of Furans.Crossref | GoogleScholarGoogle Scholar |
[3] R Banerjee, K Hks, M Banerjee, Medicinal significance of furan derivatives: A Review. Int J Res Phytochem Pharmacol 2015, 5, 48.
[4] R Marefat Seyedlar, M Imani, SM Mirabedini, Bio-based furan coatings: adhesion, mechanical and thermal properties. Polym Bull 2021, 78, 577.
| Bio-based furan coatings: adhesion, mechanical and thermal properties.Crossref | GoogleScholarGoogle Scholar |
[5] V Amarnath, K Amarnath, Intermediates in the Paal-Knorr Synthesis of Furans. J Org Chem 1995, 60, 301.
| Intermediates in the Paal-Knorr Synthesis of Furans.Crossref | GoogleScholarGoogle Scholar |
[6] AN Golonka, CS Schindler, Iron(III) chloride-catalyzed synthesis of 3-carboxy-2,5-disubstituted furans from γ-alkynyl aryl- and alkylketones. Tetrahedron 2017, 73, 4109.
| Iron(III) chloride-catalyzed synthesis of 3-carboxy-2,5-disubstituted furans from γ-alkynyl aryl- and alkylketones.Crossref | GoogleScholarGoogle Scholar |
[7] C-K Chan, Y-C Chen, Y-L Chen, M-Y Chang, Synthesis of substituted phenanthrofurans. Tetrahedron 2015, 71, 9187.
| Synthesis of substituted phenanthrofurans.Crossref | GoogleScholarGoogle Scholar |
[8] M-Y Chang, Y-C Cheng, Y-J Lu, Bi(OTf)3-Mediated Cycloisomerization of γ-Alkynyl Arylketones: Application to the Synthesis of Substituted Furans. Org Lett 2015, 17, 1264.
| Bi(OTf)3-Mediated Cycloisomerization of γ-Alkynyl Arylketones: Application to the Synthesis of Substituted Furans.Crossref | GoogleScholarGoogle Scholar |
[9] DP Pace, R Robidas, UPN Tran, CY Legault, TV Nguyen, Iodine-Catalyzed Synthesis of Substituted Furans and Pyrans: Reaction Scope and Mechanistic Insights. J Org Chem 2021, 86, 8154.
| Iodine-Catalyzed Synthesis of Substituted Furans and Pyrans: Reaction Scope and Mechanistic Insights.Crossref | GoogleScholarGoogle Scholar |
[10] Y Peng, J Luo, Q Feng, Q Tang, Understanding the Scope of Feist–Bénary Furan Synthesis: Chemoselectivity and Diastereoselectivity of the Reaction Between α-Halo Ketones and β-Dicarbonyl Compounds. Eur J Org Chem 2016, 2016, 5169.
| Understanding the Scope of Feist–Bénary Furan Synthesis: Chemoselectivity and Diastereoselectivity of the Reaction Between α-Halo Ketones and β-Dicarbonyl Compounds.Crossref | GoogleScholarGoogle Scholar |
[11] UPN Tran, G Oss, DP Pace, J Ho, TV Nguyen, Tropylium-promoted carbonyl-olefin metathesis reactions. Chem Sci 2018, 9, 5145.
| Tropylium-promoted carbonyl-olefin metathesis reactions.Crossref | GoogleScholarGoogle Scholar |
[12] G Oss, TV Nguyen, Iodonium-Catalyzed Carbonyl–Olefin Metathesis Reactions. Synlett 2019, 30, 1966.
| Iodonium-Catalyzed Carbonyl–Olefin Metathesis Reactions.Crossref | GoogleScholarGoogle Scholar |
[13] UPN Tran, G Oss, M Breugst, et al. Carbonyl–Olefin Metathesis Catalyzed by Molecular Iodine. ACS Catal 2019, 9, 912.
| Carbonyl–Olefin Metathesis Catalyzed by Molecular Iodine.Crossref | GoogleScholarGoogle Scholar |
[14] T Anh To, C Pei, RM Koenigs, T Vinh Nguyen, Hydrogen Bonding Networks Enable Bronsted Acid-Catalyzed Carbonyl-Olefin Metathesis. Angew Chem Int Ed 2022, 61, e202117366.
| Hydrogen Bonding Networks Enable Bronsted Acid-Catalyzed Carbonyl-Olefin Metathesis.Crossref | GoogleScholarGoogle Scholar |
[15] K Omoregbee, KNH Luc, AH Dinh, TV Nguyen, Tropylium-promoted prenylation reactions of phenols in continuous flow. J Flow Chem 2020, 10, 161.
| Tropylium-promoted prenylation reactions of phenols in continuous flow.Crossref | GoogleScholarGoogle Scholar |
[16] B Baghernejad, Application of p-toluenesulfonic Acid (PTSA) in Organic Synthesis. Curr Org Chem 2011, 15, 3091.
| Application of p-toluenesulfonic Acid (PTSA) in Organic Synthesis.Crossref | GoogleScholarGoogle Scholar |
[17] H Sharghi, P Shiri, M Aberi, An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes. Beilstein J Org Chem 2018, 14, 2745.
| An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes.Crossref | GoogleScholarGoogle Scholar |
[18] I Colomer, AER Chamberlain, MB Haughey, TJ Donohoe, Hexafluoroisopropanol as a highly versatile solvent. Nat Rev Chem 2017, 1, 0088.
| Hexafluoroisopropanol as a highly versatile solvent.Crossref | GoogleScholarGoogle Scholar |
[19] V Pozhydaiev, M Power, V Gandon, J Moran, D Lebœuf, Exploiting hexafluoroisopropanol (HFIP) in Lewis and Brønsted acid-catalyzed reactions. Chem Commun 2020, 56, 11548.
| Exploiting hexafluoroisopropanol (HFIP) in Lewis and Brønsted acid-catalyzed reactions.Crossref | GoogleScholarGoogle Scholar |
