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Sigma-Aldrich

Tris(dibenzylideneacetone)dipalladium(0)

97%

Synonym(s):
Pd2(dba)3, Pd2dba3
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: 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) participates in the synthesis of azepane. Crystal structure of Pd2(dba)3 has been determined by three-dimensional X-ray data. Crystals of Pd2(dba)3 are reported to crystalize in triclinic system. It is widely used Pd(0) source in Pd-mediated transformations.

Application

  • 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)


Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Reactant involved in:
  • 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

Packaging

1, 5, 25, 50, 100, 500 g in glass bottle
500 mg in glass bottle

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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

More Documents

Quotes and Ordering

Palladium-catalyzed β arylation of carboxylic esters.
Alice Renaudat et al.
Angewandte Chemie (International ed. in English), 49(40), 7261-7265 (2010-08-21)
Anant R Kapdi et al.
Journal of the American Chemical Society, 135(22), 8388-8399 (2013-05-25)
Pd(0)2(dba)3 (dba = E,E-dibenzylidene acetone) is the most widely used Pd(0) source in Pd-mediated transformations. Pd(0)2(dba-Z)3 (Z = dba aryl substituents) complexes exhibit remarkable and differential catalytic performance in an eclectic array of cross-coupling reactions. The precise structure of these
European Journal of Inorganic Chemistry, 6, 1262-1269 (2004)
Littke, A. F.; Dai, C.; Fu, G.C.
Journal of the American Chemical Society, 122, 4020-4020 (2000)
Kawatsura, M.; Hartwig, J. F.
Journal of the American Chemical Society, 121, 1473-1473 (1999)

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

Transition-Metal Catalysts

A variety of transition-metal catalysts for the Suzuki coupling reaction are now available in our catalog. The majority of these catalysts are palladium- and nickelbased, typically utilizing phosphine-derived ligands.

Heck Reaction

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes and aryl or vinyl halides (or triflates) to afford substituted alkenes.

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