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Merck
CN

225452

Bis(triphenylphosphine)palladium(II) diacetate

98%

Synonym(s):

Bis(acetato)bis(triphenylphosphine)palladium(II), Palladium(II)bis(triphenylphosphine) diacetate, Pd(OAc)2(PPh3)2

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About This Item

Linear Formula:
[(C6H5)3P]2Pd(CH3COO)2
CAS Number:
14588-08-0
Molecular Weight:
749.08
NACRES:
NA.22
PubChem Substance ID:
24853498
UNSPSC Code:
12352300
EC Number:
238-628-4
MDL number:
MFCD00010013

Key Documents

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InChI key

UVBXZOISXNZBLY-UHFFFAOYSA-L

InChI

1S/2C18H15P.2C2H4O2.Pd/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;2*1-2(3)4;/h2*1-15H;2*1H3,(H,3,4);/q;;;;+2/p-2

SMILES string

CC(=O)O[Pd]OC(C)=O.c1ccc(cc1)P(c2ccccc2)c3ccccc3.c4ccc(cc4)P(c5ccccc5)c6ccccc6

assay

98%

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

mp

136 °C (dec.) (lit.)

Application

Bis(triphenylphosphine)palladium(II) diacetate can be used as a catalyst for C-C bond formation via Sonogashira coupling, Negishi coupling, Heck coupling, and Suzuki coupling reaction.
It can also be used as a catalyst to synthesize:
  • Pyrido[1,2-a]benzimidazole derivatives by electro-oxidative intramolecular C-H/N-H annulation reaction.
  • α, β-Unsaturated carboxylic acids by hydroxycarbonylation of vinyl triflates.
  • Secondary imides by C-H functionalization of aldehydes with different N-substituted N-heteroarene-2-carboxamides.

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCJ3921
MKCG3157
MKCF5149
MKCC9767
MKCB0555V

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Palladium-catalysed hydroxycarbonylation of vinyl and aryl triflates: synthesis of α ,β-unsaturated and aromatic carboxylic acids
Cacchi S and Lupi A
Tetrahedron Letters, 33(27), 3939-3942 (1992)
Easy-separable magnetic nanoparticle-supported Pd catalysts: Kinetics, stability and catalyst re-use
Laska U, et al.
J. Catal., 268(2), 318-328 (2009)
Yus, M.; Gomis, J.
Tetrahedron Letters, 42, 5721-5721 (2001)
Palladium-Catalyzed Electro-oxidative C-H Amination toward the Synthesis of Pyrido [1, 2-a] benzimidazoles with Hydrogen Evolution
Duan Z, et al.
ACS Catalysis, 10(6), 3828-3831 (2020)
Donald Bankston et al.
The Journal of organic chemistry, 64(10), 3461-3466 (2001-10-25)
A series of crotyl ethers underwent intramolecular cyclizations in the presence of a novel catalytic couple, composed of tris(triphenylphosphine)rhodium(I) chloride and palladium(II) acetate, under Heck conditions initially described by Jeffery.(1) The data indicated that the combination of these two metal
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