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| | COPPER(II) TRIFLUOROMETHANESULFONATE Basic information | | Reaction |
| | COPPER(II) TRIFLUOROMETHANESULFONATE Chemical Properties |
| Melting point | ≥300 °C | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Water (Slightly) | | form | Powder | | color | White to slightly blue or light gray | | Water Solubility | Soluble in water. | | Sensitive | Hygroscopic | | Hydrolytic Sensitivity | 6: forms irreversible hydrate | | BRN | 4028198 | | Exposure limits | ACGIH: TWA 1 mg/m3
NIOSH: IDLH 100 mg/m3; TWA 1 mg/m3 | | Stability: | hygroscopic | | InChI | InChI=1S/2CHF3O3S.Cu/c2*2-1(3,4)8(5,6)7;/h2*(H,5,6,7);/q;;+2/p-2 | | InChIKey | SBTSVTLGWRLWOD-UHFFFAOYSA-L | | SMILES | S(=O)(=O)(O[Cu]OS(=O)(=O)C(F)(F)F)C(F)(F)F | | CAS DataBase Reference | 34946-82-2(CAS DataBase Reference) |
| Hazard Codes | C,Xi | | Risk Statements | 34 | | Safety Statements | 26-36/37/39-45-27 | | RIDADR | UN 3261 8/PG 2 | | WGK Germany | 3 | | F | 3-10 | | Hazard Note | Irritant/Hygroscopic | | TSCA | No | | HazardClass | 8 | | PackingGroup | III | | HS Code | 29049085 | | Storage Class | 11 - Combustible Solids |
| | COPPER(II) TRIFLUOROMETHANESULFONATE Usage And Synthesis |
| Reaction |
- Ring-Opening of epoxides and aziridines.
- Asymmetric conjugate addition of organozinc reagents to α,β-unsaturated ketones.
- Electrophilic addition of olefins.
- Asymmetric aziridination of olefins.
- Asymmetric cycloadditions and aldol condensations.
- Asymmetric Kharasch oxidation.
- Asymmetric Michael addition of enamides.
- Asymmetric O-H or O-R insertion reactions.
- Enantioselective intramolecular aminooxygenation of alkenes.
- Enantioselective addition of dialkylzinc reagents to N-acylpyridinium salts.
- Pd-catalyzed C-H functionalizations of oximes with arylboronic acids.
- Used as a Lewis acid in the Nazarov cyclization.
- Catalyst in the diacetoxylation olefins.
- Catalyst in the meta-selective direct arylation of α-aryl carbonyl compounds.
- Catalyst in the three-component coupling of amines, aldehydes, and alkynes.
| | Chemical Properties | white to slightly blue or light grey cryst. powder | | Uses | Copper(II) trifluoromethanesulfonate is a mild lewis acid. It is used as catalyst which promotes dehydration of alcohols and diols to alkenes at ambient temperatures. It is widely used to generate carbenoid species from -diazo esters and ketones, via in situ reduction to the Cu(I) species. It is also promotes the reaction between diazo esters and imines to give aziridines. It catalyzes syn-selective aldol condensation of (Z)-silyl enol ethers with aldehydes, Friedel-Crafts alkylation, acylation reactions of aromatics and addition of trimethylsilyl cyanide to carbonyl compounds. | | Preparation |
Copper(II) trifluoromethanesulfonate is prepared from copper(II) carbonate and triflic acid (Trifluoromethanesulfonic Acid) in MeCN.
| | reaction suitability | core: copper
reagent type: catalyst | | Purification Methods | Dissolve it in MeCN, add dry Et2O until cloudy and cool at -20o in a freezer. The light blue precipitate is collected and dried in a vacuum oven at 130o/20mm for 8hours. It has 737nm ( 22.4 max M1cm -1) in AcOH. [Salomon & Kochi J Am Chem Soc 95 330 1973]. It has also been dried in a vessel at 0.1Torr by heating with a Fischer burner [Andrist et al. J Org Chem 43 3422 1978]. It has been dried at 110-120o/5mm for 1hour before use and forms a *benzene complex which should be handled in a dry box because it is air sensitive [Kobayashi et al. Chem Pharm Bull Jpn 28 262 1980, Salomon & Kochi J Am Chem Soc 95 330 1973]. [Beilstein 3 IV 34.] |
| | COPPER(II) TRIFLUOROMETHANESULFONATE Preparation Products And Raw materials |
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