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430595

Sigma-Aldrich

Ytterbium(III) trifluoromethanesulfonate

99.99%

Synonym(s):

Yb(OTf)3, Trifluoromethanesulfonic acid ytterbium(III) salt, Yb(TFA)3, Ytterbium(III) triflate

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About This Item

Linear Formula:
(CF3SO3)3Yb
CAS Number:
54761-04-5
Molecular Weight:
620.25
MDL number:
MFCD06200261
UNSPSC Code:
12161600
PubChem Substance ID:
24866930
NACRES:
NA.22

Assay

99.99%

reaction suitability

core: ytterbium
reagent type: catalyst

SMILES string

FC(F)(F)S(=O)(=O)O[Yb](OS(=O)(=O)C(F)(F)F)OS(=O)(=O)C(F)(F)F

InChI

1S/3CHF3O3S.Yb/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3

InChI key

AHZJKOKFZJYCLG-UHFFFAOYSA-K

Related Categories

Application

A water-tolerant Lewis acid catalyst recently used in one-pot syntheses of β-lactams, and in stereocontrolled radical and nucleophilic addition reactions. Catalyzes the synthesis of deoxypenostatin A in a novel, stereoselective, intramolecular Diels-Alder reaction.
Lewis acid catalyst used with a silylated chinchona alkaloid in an asymmetric synthesis of substituted β-lactams from an acid chloride and aryl imine. Also used to catalyze an aldehyde-ene reaction in a synthesis of the guaiane skeleton.
An important Lewis acid catalyst for a variety of synthetic reactions, including allylborations.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Acyclic Stereocontrol in Radical Reactions. Diastereoselective Radical Addition/Allylation of N-Propenoyloxazolidinone.
Mukund P. Sibi et al.
The Journal of organic chemistry, 61(18), 6090-6091 (1996-09-06)
Jili Li et al.
Organic & biomolecular chemistry, 16(43), 8115-8129 (2018-10-20)
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Jason W J Kennedy et al.
The Journal of organic chemistry, 69(13), 4412-4428 (2004-06-19)
A full account of the development of the first catalytic manifold for the additions of allylboronates to aldehydes is described. The thermal additions (both diastereospecific and enantioselective) of 2-carboxyester 3,3-disubstituted allylboronates 1 to both aromatic and aliphatic aldehydes give biologically
Synlett, 3411-3411 (2006)
Tetrahedron Asymmetry, 7, 1457-1457 (1996)
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