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Sigma-Aldrich

Palladium(II) trifluoroacetate

97%

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Synonym(s):
Pd(TFA)2, Trifluoroacetic acid palladium(II) salt
Linear Formula:
(CF3COO)2Pd
CAS Number:
42196-31-6
Molecular Weight:
332.45
MDL number:
MFCD00013204
PubChem Substance ID:
24858054
NACRES:
NA.22

Quality Level

200

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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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
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)
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.
A general palladium-catalyzed sonogashira coupling of aryl and heteroaryl tosylates.
Omar R'kyek et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(33), 9986-9989 (2010-07-08)
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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