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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.
Gefahrenhinweise (EU): H314-H318
Causes severe skin burns and eye damage. Causes serious eye damage.
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