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
Pricing and availability is not currently available.

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

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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...
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...
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...
Kawatsura, M.; Hartwig, J. F.
Journal of the American Chemical Society, 121, 1473-1473 (1999)
Littke, A. F.; Dai, C.; Fu, G.C.
Journal of the American Chemical Society, 122, 4020-4020 (2000)
Articles
JosiPhos CyPF-tBu and palladium give catalyst for alkoxylation of activated heteroaryl halides with primary, secondary, and tertiary alcohols
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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.
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The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes and aryl or vinyl halides (or triflates) to afford substituted alkenes.
Read More

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