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Merck
CN

227994

Bis(dibenzylideneacetone)palladium(0)

powder

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

Key Documents

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Product Name

Bis(dibenzylideneacetone)palladium(0),

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

form

powder

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

Quality Level

100

Related Categories

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

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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Certificates of Analysis (COA)

Lot/Batch Number
MKDB1530
MKCZ8676
MKCZ5387
MKCW4974
MKCW0564

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Macsari, I.; Hupe, E.; Szabo, K. J.
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Arentsen, K.; Caddick, S.et al.
Tetrahedron Letters, 45, 3511-3511 (2004)
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