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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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
Tetrahedron Letters, 25, 4187-4187 (1984)
Keisuke Kato et al.
Angewandte Chemie (International ed. in English), 48(18), 3326-3328 (2009-02-05)
Boxing clever: Direct conversion of a terminal alkyne group into a beta-methoxyacrylate is realized with the aid of the bis(oxazoline) ligand (box). Acetyl and ketal protecting groups, free hydroxy groups, and acid-sensitive glycosidic bonds are not affected under the reaction
Mu-Wang Chen et al.
Organic letters, 12(21), 5075-5077 (2010-10-06)
An enantioselective hydrogenation of simple fluorinated imines has been developed using Pd(OCOCF(3))(2)/(R)-Cl-MeO-BIPHEP as a catalyst, and up to 94% ee was achieved. This method provides an efficient route to enantioenriched fluorinated amines.
Palladium(II)-Catalyzed Direct ortho-C-H Acylation of Anilides by Oxidative Cross-Coupling with Aldehydes using tert-Butyl Hydroperoxide as Oxidant
Chan C, et al.
Advanced Synthesis & Catalysis, 353, 2999-3006 (2011)
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