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Merck

407240

Sigma-Aldrich

Copper(I) trifluoromethanesulfonate benzene complex

technical grade, 90%

Sinónimos:

Copper(I) triflate benzene complex, Cuprous trifluoromethanesulfonate benzene complex, Trifluoromethanesulfonic acid copper(I) salt benzene complex

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About This Item

Fórmula lineal:
(CF3SO3Cu)2 · C6H6
Número de CAS:
Peso molecular:
503.34
EC Number:
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

grade

technical grade

Quality Level

assay

90%

form

powder

reaction suitability

core: copper
reagent type: catalyst

mp

160 °C (dec.) (lit.)

SMILES string

[Cu+].[Cu+].c1ccccc1.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F

InChI

1S/C6H6.2CHF3O3S.2Cu/c1-2-4-6-5-3-1;2*2-1(3,4)8(5,6)7;;/h1-6H;2*(H,5,6,7);;/q;;;2*+1/p-2

InChI key

GNXZWVVAAMVOJY-UHFFFAOYSA-L

Application

Copper(I) trifluoromethanesulfonate benzene complex can be used as a catalyst:
  • To synthesize enol-esters via copper(I) carboxylate intermediate formation.
  • In the enantioselective allylic oxidation of cyclic alkenes.
  • To prepare 2,5-disubstituted pyrrolidine derivatives from N-alkenyl, alkynyl and alkyl N-benzoyloxysulfonamides via the sulfonamidyl radical formation.

It can also be used in combination with amino acid-based chiral phosphine ligands to catalyze asymmetric conjugate additions of alkylzincs to acyclic α,β-unsaturated ketones, affording β-alkylcarbonyls in high yield and with excellent enantioselectivity.

pictograms

Flame

signalword

Warning

hcodes

Hazard Classifications

Flam. Sol. 2

Storage Class

4.1B - Flammable solid hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Visite la Librería de documentos

Enantiopure fluorous bis (oxazolines): Synthesis and applications in catalytic asymmetric reactions
Bayardon J and Sinou D
The Journal of Organic Chemistry, 69(9), 3121-3128 (2004)
Jerome Bayardon et al.
The Journal of organic chemistry, 69(9), 3121-3128 (2004-04-24)
Various enantiopure fluorous bis(oxazolines) with fluorine content between 52.7 and 58.7% have been synthesized by a simple reaction sequence that involved the introduction of two fluorinated ponytails by alkylation of the corresponding nonfluorous bis(oxazolines). These new ligands have been used
Synthesis of Enol Esters from Copper (I) Carboxylates Generated from Copper (I) Trifluoromethanesulfonate Benzene Complex
Lefler SR and Rose SD
Synthetic Communications, 29(21), 3805-3810 (1999)
Enantioselective total synthesis of erogorgiaene: applications of asymmetric Cu-catalyzed conjugate additions of alkylzincs to acyclic enones
Cesati RR, et al.
Journal of the American Chemical Society, 126(1), 96-101 (2004)
Richard R Cesati et al.
Journal of the American Chemical Society, 126(1), 96-101 (2004-01-08)
The first enantioselective synthesis of erogorgiaene (1), an inhibitor of mycobacterium tuberculosis, is disclosed. The total synthesis highlights the utility of asymmetric conjugate additions (ACA) of alkylzincs to acyclic alpha,beta-unsaturated ketones catalyzed by peptidic phosphine ligands and (CuOTf)(2).C(6)H(6). Moreover, several

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