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328774

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%

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

Certificate of Origin

Matthew H Katcher et al.
Journal of the American Chemical Society, 132(49), 17402-17404 (2010-11-23)
The enantioselective fluorination of readily available cyclic allylic chlorides with AgF has been accomplished using a Pd(0) catalyst and Trost bisphosphine ligand. The reactions proceed with unprecedented ease of operation for Pd-mediated nucleophilic fluorination, allowing access to highly enantioenriched cyclic
Martin Arthuis et al.
Chemical communications (Cambridge, England), 46(41), 7810-7812 (2010-09-21)
A novel and fully chemo- and stereoselective three component strategy leading to Z-α-chloroacrylates by a Pd(0)-catalyzed reaction of CO (1 atm) with 1,1-dichloro-1-alkenes and various alcohols is disclosed. This catalytic approach compares favourably with the Wittig type strategies as α-chloroacrylates
Kawatsura, M.; Hartwig, J. F.
Journal of the American Chemical Society, 121, 1473-1473 (1999)
Satoshi Suetsugu et al.
Organic letters, 16(3), 996-999 (2014-01-28)
The total synthesis of (-)-aurantioclavine (1) was accomplished based on an intramolecular asymmetric amination of allyl carbonate 3 containing a p-tosylamide group. The reaction using tris(dibenzylideneacetone)dipalladium(0), tBu-phosphinooxazoline, and Bu4NCl in CH2Cl2 gave azepane 2 in 77% yield with 95% enantiomeric
Tetrahedron Letters, 33, 4859-4859 (1992)

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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 Applications & Products

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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