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Merck
CN

328774

Tris(dibenzylideneacetone)dipalladium(0)

97%, powder

Synonym(s):

Pd2dba3, Pd2(dba)3

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About This Item

Linear Formula:
(C6H5CH=CHCOCH=CHC6H5)3Pd2
CAS Number:
51364-51-3
Molecular Weight:
915.72
UNSPSC Code:
12161600
PubChem Substance ID:
24859746
NACRES:
NA.22
MDL number:
MFCD00013310

Key Documents

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Product Name

Tris(dibenzylideneacetone)dipalladium(0), 97%

SMILES string

[Pd].[Pd].O=C(\C=C\c1ccccc1)/C=C/c2ccccc2.O=C(\C=C\c3ccccc3)/C=C/c4ccccc4.O=C(\C=C\c5ccccc5)/C=C/c6ccccc6

InChI

1S/3C17H14O.2Pd/c3*18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;;/h3*1-14H;;/b3*13-11+,14-12+;;

InChI key

CYPYTURSJDMMMP-WVCUSYJESA-N

assay

97%

form

powder

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

152-155 °C (lit.)

Quality Level

200

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Application

    Application Guide for Palladium Catalyzed Cross-Coupling Reactions

    Reactant involved in:

    • Synthesis of azepanes
    • Synthesis of nanosized palladium phosphides upon interaction with white phosphorous
    • Preparation of palladium triphenylphosphine carbonyl cluster complexes
    • Precursor for synthesis of functionalized multiwalled carbon nanotube-palladium complexes used as catalysts for Heck coupling reactions
    • Selective carbon-sulfur bond formation via addition of S-S and S-H bonds to alkynes


    Catalyst for:

    • Suzuki cross-coupling reactions
    • PCN- and PCS-pincer palladium complex catalyzed tandem allylation
    • Catalyst for Suzuki coupling of aryl chlorides (eq. 1)
    • Catalyst for Heck coupling of aryl chlorides (eq. 2)
    • Catalyst for arylation of ketones (eq. 3)
    • Catalyst for Buchwald-Hartwig amination of aryl halides (eq. 4)
    • Catalyst for fluorination of allylic chlorides (eq. 5)
    • Catalyst for β-arylation of carboxylic esters (eq. 6)
    • Catalyst for carbonylation of 1,1-dichloro-1-alkenes (eq. 7)
    • Catalyst for conversion of aryl and vinyl triflates to aryl and vinyl halides (eq. 8)
    • Pd source for enantioselective Tsuji Allylations

General description

Tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) is a versatile compound widely used as a Pd(0) source in various Pd-mediated transformations. Pd2(dba)3 is known for its high reactivity and ability to facilitate oxidative addition reactions. It is prepared by reacting palladium salts with dibenzylideneacetone ligands. It acts as a catalyst for several reactions including Suzuki cross-coupling, Heck coupling, arylation, Buchwald-Hartwig amination, and fluorination. It is often used in catalytic amounts and has been shown to be effective in promoting coupling reactions between aryl halides and boronic acids.

For small scale and high throughput uses, product is also available as ChemBeads (919772)

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

hcodes

H317,H411

Hazard Classifications

Aquatic Chronic 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 2

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
MKCZ4728
MKCX7218
MKCX8106
MKCX4171
MKCW4401

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Crystal and molecular structure of tris (dibenzylideneacetone) dipalladium (0).
Pierpont CG and Mazza MC
Inorganic Chemistry, 13(8), 1891-1895 (1974)
Wolfe, J. P.; Wagaw, S.; Buchwald, S. L.
Journal of the American Chemical Society, 118, 7215-7215 (1996)
Catalysts for Suzuki?Miyaura Coupling Processes:? Scope and Studies of the Effect of Ligand Structure
Timothy E. Barder, Shawn D. Walker, Joseph R. Martinelli, and Stephen L. Buchwald
Journal of the American Chemical Society, 127(13), 4685?4696-4685?4696 (2005)
The Reaction Mechanism of the Enantioselective Tsuji Allylation: Inner-Sphere and Outer-Sphere Pathways, Internal Rearrangements, and Asymmetric C?C Bond Formation
John A. Keith, Douglas C. Behenna, et al.
Journal of the American Chemical Society, 134(46) , 19050?19060-19050?19060 (2012)
Tetrahedron Letters, 33, 4859-4859 (1992)
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