Bis(dibenzylideneacetone)palladium CAS 32005-36-0

Introduction：Basic information about Bis(dibenzylideneacetone)palladium CAS 32005-36-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Bis(dibenzylideneacetone)palladium Basic information

• Product Name: Bis(dibenzylideneacetone)palladium
• Synonyms: BIS(DIBENZYLIDENEACETONE)PALLADIUM;BIS(DIBENZYLIDENEACETONE) PALLADIUM(0);PALLADIUM (0) BIS(DIBENZYLIDENEACETONE) SALT;PALLADIUM(0) BIS(DIBENZYLIDENEACETONE);PD(DBA)2;Bis(dibenzylideneacetone)palladium(0) Pd(dba)2Pd2(dba)3dba;BIS(DIBENZYLIDENEACETONE)PALLADIUM(O);Bis(dibenzylideneacetone)palladium(0) Pd(dba)2Pd2(dba)3ba
• CAS: 32005-36-0
• MF: C34H20O2Pd
• MW: 566.95
• EINECS: 608-691-6
• Product Categories: chemical reaction,pharm,electronic,materials;organometallic complex;Catalysts for Organic Synthesis;Classes of Metal Compounds;Catalysts-Ligands;Pd;Homogeneous Catalysts;Metal Complexes;Pd (Palladium) Compounds;Synthetic Organic Chemistry;Transition Metal Compounds
• Mol File: 32005-36-0.mol

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
• InChI: InChI=1S/2C17H10O.Pd/c2*18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;/h2*1-10H;
• InChIKey: WTAPZWXVSZMMDG-JZOPPWQGSA-N
• SMILES: O=C1C2=C(C3C=CC=CC=3)[Pd]34562(C(C2C=CC=CC=2)=C3C(=O)C4=C5C2C=CC=CC=2)C(C2C=CC=CC=2)=C16
• CAS DataBase Reference: 32005-36-0(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
• Storage Class: 11 - Combustible Solids

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.

Chemical Properties

purple brown

Uses

Hydrogenation, 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.

Uses

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

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.

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.

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

Synthesis

Bis(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 materials: Methanol-->Toluene-->Acetone-->Acetonitrile-->Sodium acetate-->Benzaldehyde-->Palladium chloride-->1,3-Dichloropropane
• Preparation Products: trans-Bis(triphenylphosphine)palladium dichloride-->Bis[Tris(2-methylphenyl)phosphine]palladium