Copper(II) trifluoromethanesulfonate

• Catalog: OFC34946822
• CAS: 34946-82-2
• Category: Fluorinated Metal Complexes
• Synonyms: Copper(II) Triflate
• Purity: 99%
• MDL Number: MFCD00077492

• IUPAC Name: copper;trifluoromethanesulfonate
• InChI: InChI=1S/2CHF3O3S.Cu/c2*2-1(3,4)8(5,6)7;/h2*(H,5,6,7);/q;;+2/p-2
• InChI Key: SBTSVTLGWRLWOD-UHFFFAOYSA-L
• Isomeric SMILES: C(F)(F)(F)S(=O)(=O)[O-].C(F)(F)(F)S(=O)(=O)[O-].[Cu+2]
• EC Number: 252-300-8

• Molecular Formula: C2CuF6O6S2
• Molecular Weight: 361.68
• Appearance: Light green solid
• Stability: Air sensitive

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 0
• Exact Mass: 360.833646 g/mol
• Monoisotopic Mass: 360.833646 g/mol
• Topological Polar Surface Area: 131Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 145

Case Study

Copper(II) Trifluoromethanesulfonate Catalyzed Cascade Synthesis of Nitrogen-Rich Tetracycles

Liu L, et al. European Journal of Organic Chemistry, 2016, 2016(22), 3684-3690.

Copper(II) trifluoromethanesulfonate (Cu(OTf)₂) effectively catalyzes a hydroamination-cyclization-dimerization cascade of homopropargylic amines, enabling the one-pot construction of complex nitrogen-containing tetracycles. The transformation begins with Cu(OTf)₂-promoted intramolecular radical hydroamination of the terminal alkyne, yielding a cyclic amine intermediate. This species undergoes further cyclization and dimerization via a Povarov-type [4+2] reaction with a second intermediate, forming four new bonds and five stereocenters in a single step.
The reaction is typically performed using 10 mol% Cu(OTf)₂ in dichloroethane at 60 °C, proceeding smoothly without additional oxidants. This method enables rapid access to polycyclic frameworks and was successfully applied to synthesize the aglycon core of incargranine B. The dual role of Cu(OTf)₂-as a Lewis acid and radical initiator-proves essential for orchestrating the cascade sequence.

Copper(II) Trifluoromethanesulfonate-Catalyzed Synthesis of 2-Methyl-1,5-Diaryl-1H-Pyrroles via One-Pot Multicomponent Heterocyclization

Xu C, et al. Tetrahedron Letters, 2018, 59(3), 260-263.

In this study, Copper(II) trifluoromethanesulfonate [Cu(OTf)₂] demonstrates high catalytic efficiency in a one-pot, three-component reaction enabling the synthesis of 2-methyl-1,5-diaryl-1H-pyrroles. The protocol employs readily available starting materials-substituted styrenes, acetone, and arylamines-and leverages oxidative catalysis and subsequent heterocyclization under mild thermal conditions.
The reaction is catalyzed by 5 mol% Cu(OTf)₂ in combination with 5 mol% MnCl₂·4H₂O and uses tert-butyl hydroperoxide (TBHP) as the oxidant, DBU as a base, and sulfamic acid (HSO₃NH₂) as a nitrogen source under air at 60 °C for 24 hours. Acetone functions both as a solvent and a carbonyl source, facilitating in situ formation of a 1,4-dicarbonyl intermediate that undergoes Paal-Knorr-type pyrrole ring construction with the arylamine. The optimized conditions accommodate a broad range of arylamines and styrenes, affording the desired 2-methyl-1,5-diaryl-1H-pyrroles in moderate to good isolated yields (41-69%).