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Sigma-Aldrich

Tris(dibenzylideneacetone)dipalladium(0)

97%

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Synonym(s):
Pd2dba3, Pd2(dba)3
Linear Formula:
(C6H5CH=CHCOCH=CHC6H5)3Pd2
CAS Number:
Molecular Weight:
915.72
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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.)

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

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This Item
683345697265227994
vibrant-m

683345

[Pd2(dba)3] x dba

reaction suitability

core: palladium, reaction type: Cross Couplings, reaction type: Hiyama Coupling, reaction type: Sonogashira Coupling, reaction type: Suzuki-Miyaura Coupling, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Negishi Coupling, reagent type: catalyst, reaction type: Stille Coupling, reaction type: Heck Reaction

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 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 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

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

form

powder

form

powder

form

crystals

form

powder

mp

152-155 °C (lit.)

mp

152-155 °C (lit.)

mp

-

mp

-

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)

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

pictograms

Exclamation markEnvironment

signalword

Warning

Hazard Classifications

Aquatic Chronic 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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)
European Journal of Organic Chemistry, 10, 2214-2222 (2004)
Tetrahedron Letters, 33, 4859-4859 (1992)
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)
Wolfe, J. P.; Wagaw, S.; Buchwald, S. L.
Journal of the American Chemical Society, 118, 7215-7215 (1996)

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