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Copper(II) trifluoromethanesulfonate acts as a catalyst in Diels-Alder reaction and cyclopropanation reactions. It is also used as a reagent for oligosaccharide synthesis. It acts as a Lewis acid. It is also employed in the dimerization of ketone enolates and tetramethylsilane enol ethers. It is used to prepare cis vinylic sulfones and oxazoles from alkynyl sulfones and ketones respectively. Further, it plays an important role for cyclization of dienolates. In addition to this, it is useful for dehydration of alcohols.
Mild Lewis acid:
Used catalytically, promotes dehydration of alcohols and diols to alkenes at ambient temperatures: Helv. Chim. Acta, 70, 607 (1987).
Widely used to generate carbenoid species from ɑ-diazo esters and ketones, via in situ reduction to the Cu(I) species: J. Am. Chem. Soc., 95, 3300 (1973). Preferred reagent for intramolecular cyclization of various diazo ketones: J. Org. Chem., 49, 11496 (1984). Also promotes the reaction between diazo esters and imines to give aziridines: J. Chem. Soc., Chem. Commun., 1 (1995).
Catalyzes syn-selective aldol condensation of (Z)-silyl enol ethers with aldehydes: Chem. Lett., 959 (1997).
Friedel-Crafts alkylation and acylation reactions of aromatics are also catalyzed: Tetrahedron, 57, 241 (2001).
For a brief feature on uses of the reagent in synthesis, see: Synlett, 1044 (2005).
Balaso, G. J.; Ashish, A. V.; Shriniwas, D. S. Copper(II)triflate Promoted Highly Chemoselective Rearrangement of Chalcone Epoxides to beta-keto Aldehydes. Lett. Org. Chem. 2015, 12 (1), 55-61.
Jha, M.; Shelke, G. M.; Pericherla, K.; Kumar, A. Microwave assisted copper triflate-catalyzed rapid hydration of aryl acetylenes. Tetrahedron Lett. 2014, 55 (34), 4814-4816.
Hazard Statements: H314
Causes severe skin burns and eye damage.
Precautionary Statements: P260-P264b-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant