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227994 Sigma-Aldrich

Bis(dibenzylideneacetone)palladium(0)

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

  • CAS Number 32005-36-0

  • Linear Formula (C6H5CH=CHCOCH=CHC6H5)2Pd

  • Molecular Weight 575.00

  •  MDL number MFCD00051942

  •  PubChem Substance ID 24853668

  •  NACRES NA.22

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Properties

Related Categories Catalysis, Catalysis and Inorganic Chemistry, Chemical Synthesis, Development Quantities for Research, Homogeneous Pd Catalysts,
Quality Level   100
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
storage temp.   room temp
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

Description

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.

Packaging

2, 5, 50 g in glass bottle

500 mg in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

Heck Reaction

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes, and aryl or vinyl halides (or triflates) to afford substituted alkenes.1,2 It is a useful carbon–carbon bond form...
Keywords: Asymmetric synthesis, Cancer, Catalysis, Coupling reactions, Cross couplings, Heck Reaction, Herbicides, Ligands, Organic synthesis, Solvents

Related Content

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Palladium catalyzed cross-coupling reactions have revolutionized the way in which molecules are constructed. From the fields of organic synthesis and medicinal chemistry, to materials science and pol...
Keywords: Catalysis, Coupling reactions, Cross couplings, Materials Science, Medicinal chemistry, Organic synthesis, Polymer science, transformation

Peer-Reviewed Papers
15

References

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