Yttrium triflate
| Names | |
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| IUPAC name
tris(trifluoromethanesulfonate);yttrium(3+)
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Other names
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.156.916 |
| EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C3F9O9S3Y | |
| Molar mass | 536.10 g·mol−1 |
| Appearance | colorless solid |
| Density | 1.7 g/cm3 |
| Melting point | 300 °C (572 °F; 573 K) |
| soluble | |
| Hazards | |
| GHS labelling:[1] | |
| Warning | |
| H315, H319, H335 | |
| P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Yttrium triflate is a complex inorganic compound of yttrium, fluorine, carbon, sulphur, and oxygen with the chemical formula (CF3SO3)3Y.[2] This is the yttrium(III) salt of triflic acid.[3]
Properties
The compound forms a colorless solid that is highly hygroscopic and forms hydrates. It is soluble in water and soluble in polar organic solvents such as acetonitrile, THF, and methanol.
Yttrium triflate is a specialised Lewis acid catalyst widely used in organic synthesis, particularly in carbon–carbon bond-forming reactions such as the aldol reactions, Diels–Alder cycloaddition, and Friedel–Crafts acylations.[4][5] It is valued for its stability in water and resistance to decomposition, in contrast to traditional Lewis acids like aluminium trichloride or boron trifluoride.[6]
Synthesis
Yttrium triflate is prepared from yttrium(III) oxide and 50% aqueous trifluoromethanesulfonic acid.[7]
- Y2O3 + 6CF3SO3H → 2Y(CF3SO3)3 + 3H2O
The product is crystallised from water or an organic solvent and can be dried to remove excess water.
Alternatively, the compound may be synthesised from yttrium(III) chloride and silver triflate, but the oxide method is preferred for large-scale preparation.
Uses
The compound catalyzes aldol reactions and cycloadditions. It can be fixed to silica to obtain a heterogeneous catalyst for Michael additions and Diels-Alder reactions.[8] Other reactions catalyzed by yttrium triflate include the polymerization of caprolactone[9], the trimerization of nitriles to triazines[10], and the addition of amines to nitriles to form amidines.[11]
References
- ^ PubChem. "Yttrium trifluoromethanesulfonate". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-05-16.
- ^ "Yttrium Trifluoromethanesulfonate". American Elements. Retrieved 14 May 2026.
- ^ "Yttrium(III) trifluoromethanesulfonate". Sigma Aldrich. Retrieved 14 May 2026.
- ^ Parvulescu, Vasile I.; Kemnitz, Erhard (28 January 2016). New Materials for Catalytic Applications. Elsevier. p. 232. ISBN 978-0-444-63588-4. Retrieved 18 May 2026.
- ^ Charette, André B. (15 July 2015). Handbook of Reagents for Organic Synthesis: Reagents for Heteroarene Functionalization. John Wiley & Sons. p. 711. ISBN 978-1-118-72655-6. Retrieved 14 May 2026.
- ^ De, Surya Kanta (March 2004). "Yttrium triflate as an efficient and useful catalyst for chemoselective protection of carbonyl compounds". Tetrahedron Letters. 45 (11): 2339–2341. doi:10.1016/j.tetlet.2004.01.106. Retrieved 14 May 2026.
- ^ Palmer, Leoni I.; Read de Alaniz, Javier (15 March 2012). "Yttrium Trifluoromethanesulfonate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289x.rn01416. ISBN 978-0-471-93623-7.
- ^ Donato, Emanuela; Medici, Fabrizio; Chiroli, Valerio; Rossi, Sergio; Puglisi, Alessandra (December 2023). "Recoverable and reusable heterogeneous yttrium triflate for michael and diels-alder additions". Tetrahedron Green Chem. 2 100032. doi:10.1016/j.tgchem.2023.100032. hdl:2434/1031209.
- ^ Kunioka, Masao; Wang, Yi; Onozawa, Shun-ya (May 2003). "Polymerization of Poly(ε-caprolactone) Using Yttrium Triflate". Polymer Journal. 35 (5): 422–429. doi:10.1295/polymj.35.422. Retrieved 14 May 2026.
- ^ Díaz-Ortiz, Angel; de la Hoz, Antonio; Moreno, Andrés; Sánchez-Migallón, Ana; Valiente, Gema (2002). "Synthesis of 1,3,5-triazines in solvent-free conditions catalysed by silica-supported lewis acids". Green Chem. 4 (4): 339–343. doi:10.1039/B202014A.
- ^ Forsberg, John H.; Spaziano, Vincent T.; Balasubramanian, Trichey M.; Liu, Gordon K.; Kinsley, Steven A.; Duckworth, Charles A.; Poteruca, John J.; Brown, Paul S.; Miller, Judith L. (March 1987). "Use of lanthanide(III) ions as catalysts for the reactions of amines with nitriles". The Journal of Organic Chemistry. 52 (6): 1017–1021. doi:10.1021/jo00382a009.