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Sigma-Aldrich

Tetrakis(pyridine)copper(II) triflate

95%

Synonym(s):

[Cu(OTf)2(py)4], Cu(pyridine)4(OTf)2, Tetrakis(pyridine)copper(II) bis(trifluoromethanesulfonate)

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About This Item

Empirical Formula (Hill Notation):
C22H20CuF6N4O6S2
CAS Number:
Molecular Weight:
678.08
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

95%

form

crystals

reaction suitability

core: copper
reagent type: catalyst

mp

190-194 °C

storage temp.

−20°C

SMILES string

c1ccncc1.c2ccncc2.c3ccncc3.c4ccncc4.FC(F)(F)S(=O)(=O)O[Cu]OS(=O)(=O)C(F)(F)F

InChI

1S/4C5H5N.2CHF3O3S.Cu/c4*1-2-4-6-5-3-1;2*2-1(3,4)8(5,6)7;/h4*1-5H;2*(H,5,6,7);/q;;;;;;+2/p-2

InChI key

DOUMBTAZXRQKGF-UHFFFAOYSA-L

Application

Tetrakis(pyridine)copper(II) triflate [Cu(OTf)2(py)4] is a general copper-based catalyst. It is commonly used to catalyze copper-mediated radiofluorination of arenes and heteroarene. It is also employed in C(sp3)-H functionalization/cyclisation of 2-amino-N,N-dialkylbenzamides to synthesize 2,3-disubstituted-4(3H)-quinazolinones.
Tetrakis(pyridine)copper(II) triflate can be used to catalyze:
  • Intra and intermolecular aziridination of allylic carbamates and styrenes.
  • 18F-fluorination of aryl boronic esters to generate fluroarenes applicable as radiotracers.
  • Nucleophilic radiobromination of aryl borons with a radiobromide ion applicable in the preparation of radiobrominated pharmaceuticals.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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A general copper?mediated nucleophilic 18F fluorination of arenes.
Tredwell M, et al.
Angewandte Chemie (Weinheim an der Bergstrasse, Germany), 126(30), 7885-7889 (2014)
Copper-catalyzed alkene aziridination with N-tosyloxycarbamates
Lebel H, et al.
Organic Letters, 9(23), 4797-4800 (2007)
Copper-catalyzed C?H functionalization reactions: Efficient synthesis of heterocycles.
Guo X X, et al.
Chemical Reviews, 115(3), 1622-1651 (2014)
Pyrazine and pyridine complexes of copper (II) trifluoromethanesulfonate. Crystal structure of tetrakis (pyridine) bis (trifluoromethanesulfonato-O) copper (II) and magnetic exchange in (pyrazine) bis (trifluoromethanesulfonato-O) copper (II).
Haynes J S, et al.
Inorganic Chemistry, 27(7), 1237-1241 (1988)
Enhanced copper-mediated 18 F-fluorination of aryl boronic esters provides eight radiotracers for PET applications
Preshlock S, et al.
Chemical Communications (Cambridge, England), 52(54), 8361-8364 (2016)

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