Skip to Content
Merck
All Photos(6)

Key Documents

View All Documentation

Safety Information

227994

Sigma-Aldrich

Bis(dibenzylideneacetone)palladium(0)

Synonym(s):

Palladium(0) bis(dibenzylideneacetone), Pd(dba)2

Sign Into View Organizational & Contract Pricing
All Photos(6)

About This Item

Linear Formula:
(C6H5CH=CHCOCH=CHC6H5)2Pd
CAS Number:
32005-36-0
Molecular Weight:
575.00
MDL number:
MFCD00051942
UNSPSC Code:
12161600
PubChem Substance ID:
24853668
NACRES:
NA.22

form

powder

Quality Level

100

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

SMILES string

[Pd].O=C(/C=C/c1ccccc1)\C=C\c2ccccc2.O=C(/C=C/c3ccccc3)\C=C\c4ccccc4

InChI

1S/2C17H14O.Pd/c2*18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;/h2*1-14H;/b2*13-11+,14-12+;

InChI key

UKSZBOKPHAQOMP-SVLSSHOZSA-N

General description

Bis(dibenzylideneacetone)palladium(0) (Pd(dba)2) is an air stable Pd0 complex. It is a reagent for the synthesis of allylic substituted cyclopentadienes. It is a homogeneous catalyst. It catalyzes the alkylation of allyl acetates by various nucleophiles under mild conditions.

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Bis(dibenzylideneacetone)palladium(0) (Pd(dba)2) was employed as catalyst in the following studies:
  • Synthesis of isomeric 2-aryl-2,5-dihydrofurans, via Heck coupling of aryl bromides with alkenes using neopentyl phosphine ligands.
  • Heck reaction of benzyl trifluoroacetate and 2,3-dihydrofuran phosphoramidite ligand.
  • Allylation of stabilized anions.
  • Cross coupling of allyl, alkenyl and aryl halides with organostannanes.
  • Cross coupling of vinyl halides with alkenyl zinc species.
  • Carbonylation of alkenyl and aryl halides.
  • Employed with cyclic thiourea ligands in an efficient aerobic oxidation of alcohols to aldehydes and ketones.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

227994-50G:
227994-VAR-9:
227994-BULK-9:
227994-VAR:
227994-BULK:
227994-2G:
227994-500MG:
227994-5G:

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCQ3487
MKCN6090
MKCM2583
MKCK9489
MKCK3628

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Xiaoxiang Liu et al.
Journal of the American Chemical Society, 126(16), 5182-5191 (2004-04-22)
A general procedure for the palladium-catalyzed arylation of trimethylsilyl enolates of esters and imides is reported. In the presence of ZnF2 or Zn(O-t-Bu)2 as an additive, the trimethylsilyl enolates of esters, including those bearing alpha-alkoxy derivatives, underwent arylation in high
Bis (dibenzylideneacetone) palladium (0).
Stille JR, et al.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2013)
Zhigang Yang et al.
Journal of the American Chemical Society, 134(29), 11833-11835 (2012-07-04)
We report herein the first examples of asymmetric Mizoroki-Heck reactions using benzyl electrophiles. A new phosphoramidite was identified to be an effective chiral ligand in the palladium-catalyzed reaction. The reaction is compatible with polar functional groups and can be readily
Tetrahedron Letters, 22, 1399-1399 (1981)
Cuerva, J. M.; Gomez-Bengoa, E.; et al
The Journal of Organic Chemistry, 62, 7540-7540 (1997)
View All Related Papers

Articles

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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service