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Sigma-Aldrich

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
EC Number:
238-628-4
MDL number:
MFCD00010013
UNSPSC Code:
12352300
PubChem Substance ID:
24853498
NACRES:
NA.22

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.)

SMILES string

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

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

InChI key

UVBXZOISXNZBLY-UHFFFAOYSA-L

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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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Easy-separable magnetic nanoparticle-supported Pd catalysts: Kinetics, stability and catalyst re-use
Laska U, et al.
J. Catal., 268(2), 318-328 (2009)
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)
Cross coupling reactions catalyzed by (NHC) Pd (II) complexes
GURBUZ N, et al.
Turkish Journal of Chemistry, 39(6), 1115-1157 (2015)
Jang, M.-Y.; De Jonghe, S.; et al.
Tetrahedron Letters, 47, 8917-8917 (2006)
Gary A Molander et al.
Journal of the American Chemical Society, 126(33), 10313-10318 (2004-08-19)
A formal total synthesis of oximidine II has been achieved, employing a Suzuki-type coupling approach to construct the highly strained, polyunsaturated 12-membered macrolactone. To achieve this goal, benefit was derived from the stability of potassium alkenyltrifluoroborates to establish conditions for
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