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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
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Product Name

Tris(dibenzylideneacetone)dipalladium(0), 97%

Quality Level

200

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

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
GHS07,GHS09

signalword

Warning

hcodes

H317,H411

Hazard Classifications

Aquatic Chronic 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

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
MKCQ7655
MKCQ7654
MKCP9817
MKCP8744
MKCN8471

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Articles

C-O Cross-Coupling of Activated Aryl and Heteroaryl Halides with Aliphatic Alcohols

JosiPhos CyPF-tBu and palladium give catalyst for alkoxylation of activated heteroaryl halides with primary, secondary, and tertiary alcohols

Related Content

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)
Tetrahedron Letters, 33, 4859-4859 (1992)
View All Related Papers

Global Trade Item Number

SKUGTIN
328774-1G04061826717776
328774-500MG04061826717790
328774-100G04061833546635
328774-25G04061826717783
328774-500G04061833498965
328774-50G04061826717806
328774-5G04061826717813