Bis(dibenzylideneacetone)palladium

Bis(dibenzylideneacetone)palladium Basic information
Reaction
Product Name:Bis(dibenzylideneacetone)palladium
Synonyms:BIS(DIBENZYLIDENEACETONE)PALLADIUM;BIS(DIBENZYLIDENEACETONE) PALLADIUM(0);PALLADIUM (0) BIS(DIBENZYLIDENEACETONE) SALT;Bis(dibenzylideneacetone)palladium(0) Pd(dba)2Pd2(dba)3dba;BIS(DIBENZYLIDENEACETONE)PALLADIUM(O);Bis(dibenzylideneacetone)palladium(0) Pd(dba)2Pd2(dba)3ba;Bis(dibenzylideneacetone)palladium(O) Can be used to form catalysts in situ by separate addition of ligand. 135 dec.;Bis(dibenzylideneacetone)pall
CAS:32005-36-0
MF:C34H20O2Pd
MW:566.95
EINECS:608-691-6
Product Categories:chemical reaction,pharm,electronic,materials;organometallic complex;Catalysts-Ligands;Pd;Catalysts for Organic Synthesis;Classes of Metal Compounds;Homogeneous Catalysts;Metal Complexes;Pd (Palladium) Compounds;Synthetic Organic Chemistry;Transition Metal Compounds
Mol File:32005-36-0.mol
Bis(dibenzylideneacetone)palladium Structure
Bis(dibenzylideneacetone)palladium Chemical Properties
Melting point 150°C
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
solubility Chloroform (Slightly)
form Fine Powder
color Red-brown to black
Water Solubility insoluble
Sensitive Air & Moisture Sensitive
Stability:Hygroscopic
InChIKeyWTAPZWXVSZMMDG-JZOPPWQGSA-N
CAS DataBase Reference32005-36-0(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/38
Safety Statements 22-24/25-37/39-26
WGK Germany 3
TSCA No
HS Code 28439000
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Bis(dibenzylideneacetone)palladium Usage And Synthesis
Reaction
  1. Palladium-catalyzed acylation of unsaturated halides by anions of enol ethers.
  2. Asymmmetric Allylation reactions.
  3. Intramolecular reactions with alkenes.
  4. Carbonylation reactions.
  5. Cross Coupling reactions.
Reactions of 32005-36-0_1
Reactions of 32005-36-0_2
Reactions of 32005-36-0_3

Chemical Propertiespurple brown
UsesHydrogenation, isomerization, carbonylation, oxidation, C-C bond formation.Bis(dibenzylideneacetone)palladium(0) is used as a reagent for the preparation of allylic substituted cyclopentadienes. It acts as a homogeneous catalyst as well as in the alkylation of allyl acetates by various nucleophiles. Further, it is used in Suzuki reaction.
UsesApplication Guide for Palladium Catalyzed Cross-Coupling Reactions
ApplicationBis(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.
General DescriptionBis(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.
SynthesisBis(dibenzylideneacetone)palladium(0) was prepared by reduction of PdCl2 with methanol in the presence of sodium acetate and dibenzylideneacetone, as dark-violet pre-cipitate with mp 152°C (150°C ). 
Bis(dibenzylideneacetone)palladium Preparation Products And Raw materials
Raw materialsMethanol-->Toluene-->Acetone-->Acetonitrile-->Sodium acetate-->Benzaldehyde-->Palladium chloride-->1,3-Dichloropropane
Preparation Productstrans-Bis(triphenylphosphine)palladium dichloride-->Bis[Tris(2-methylphenyl)phosphine]palladium
BIS(DI-TERT-BUTYLPHOSPHINO)METHANE Bis[1,2-bis(diphenylphosphino)ethane]palladium(0) DICHLOROBIS(METHYLDIPHENYLPHOSPHINE)PALLADIUM(II) A Ten.JPC palladium carbon fine chemical catalyzer Bis[Tris(2-methylphenyl)phosphine]palladium Bis(2,4-pentanedionato-O,O')palladium(II) Bis(2-dicyclohexylphosphinophenyl)ether, 98% BIS(TRIPHENYLPHOSPHINE)COBALT (II) CHLORIDE DICHLOROBIS(CHLORODI-TERT-BUTYLPHOSPHINE) PALLADIUM (II) Dichloro(1,5-cyclooctadiene)platinum(II) Bis[rhodium(α,α,α′,α′-tetramethyl-1,3-benzenedipropionic acid) Platinum bis(acetylacetonate) Tris(dibenzylideneacetone)dipalladium Tris(dibenzylideneacetone)dipalladium-chloroform adduct Dibenzylideneacetone Bis(dibenzylideneacetone)palladium Tris(dibenzylideneacetone)dipalladium Bis(dibenzylideneacetone)palladium(0)~Pd_2(dba)_3

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