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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

Quality Level

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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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

Signal Word

Warning

Hazard Statements

Hazard Classifications

Aquatic Chronic 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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

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