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Bis(dibenzylideneacetone)palladium(0)

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Synonym(s):
Palladium(0) bis(dibenzylideneacetone), Pd(dba)2
Linear Formula:
(C6H5CH=CHCOCH=CHC6H5)2Pd
CAS Number:
Molecular Weight:
575.00
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

powder

Quality Level

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

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328774711071366315
form

powder

form

powder

form

powder

form

solid

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

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

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Tetrahedron Letters, 22, 1399-1399 (1981)
Cuerva, J. M.; Gomez-Bengoa, E.; et al
The Journal of Organic Chemistry, 62, 7540-7540 (1997)
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
Bis (dibenzylideneacetone) palladium (0).
Stille JR, et al.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2013)
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

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