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299685

Sigma-Aldrich

Palladium(II) trifluoroacetate

97%

Synonym(s):

Pd(TFA)2, Trifluoroacetic acid palladium(II) salt

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About This Item

Linear Formula:
(CF3COO)2Pd
CAS Number:
42196-31-6
Molecular Weight:
332.45
MDL number:
MFCD00013204
UNSPSC Code:
12161600
PubChem Substance ID:
24858054
NACRES:
NA.22

Assay

97%

form

solid

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: catalyst
reaction type: C-H Activation

mp

~220 °C

SMILES string

FC(F)(F)C(=O)O[Pd]OC(=O)C(F)(F)F

InChI

1S/2C2HF3O2.Pd/c2*3-2(4,5)1(6)7;/h2*(H,6,7);/q;;+2/p-2

InChI key

PBDBXAQKXCXZCJ-UHFFFAOYSA-L

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General description

Palladium(II) trifluoroacetate is a catalyst used in Suzuki-Miyaura, Heck, and Stille cross-coupling reactions.

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Catalyst used for the mild decarboxylation of electron-rich aromatic acids and the direct cross-coupling of unactivated arenes.
Catalyzes the selective allylic oxidation of geranylacetone and other olefins to their allyl acetates, which can then be converted to keto alcohols.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ5496
MKCQ9029
MKCP8840
MKCN7259
MKCN2501

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Tetrahedron Letters, 25, 4187-4187 (1984)
John E Bercaw et al.
The Journal of organic chemistry, 73(21), 8654-8657 (2008-09-30)
Molecular oxygen can replace sacrificial olefins as the hydrogen acceptor in the palladium trifluoroacetate catalyzed dehydrogenation of cyclohexene and related cyclic olefins into aromatics. One of the major drawbacks of the homogeneous system is the tendency of the palladium trifluoroacetate
Joshua S Dickstein et al.
Organic letters, 9(13), 2441-2444 (2007-06-05)
A palladium-catalyzed aromatic decarboxylation reaction has been developed. With electron-rich aromatic acids, the reaction proceeds efficiently under fairly mild conditions in good yields. The method was useful with complex functionalized substrates containing hindered carboxylic acids.
David R Stuart et al.
Science (New York, N.Y.), 316(5828), 1172-1175 (2007-05-26)
The industrially important coupling of aromatic compounds has generally required differential prefunctionalization of the arene coupling partners with a halide and an electropositive group. Here we report that palladium, in conjunction with a copper oxidant, can catalyze the cross-coupling of
Modular synthesis of 1,2-diamine derivatives by palladium-catalyzed aerobic oxidative cyclization of allylic sulfamides.
Richard I McDonald et al.
Angewandte Chemie (International ed. in English), 49(32), 5529-5532 (2010-06-29)
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