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227994

Bis(dibenzylideneacetone)palladium(0)

powder

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Synonym(s):

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

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About This Item

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

Bis(dibenzylideneacetone)palladium(0),

form

powder

Quality Segment

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

greener alternative product characteristics

Catalysis
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Aligned

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

We are committed to bringing you Greener Alternative Products, which adhere to one or more of the 12 Principles of Green Chemistry. This palladium source generates catalytically active Pd(0) species in situ for cross-coupling reactions. Its versatility in Buchwald-Hartwig aminations enables efficient carbon-heteroatom bond formation with high selectivity. Click here for more information.
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.
Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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