227994

Bis(dibenzylideneacetone)palladium(0)

• Synonym(s): Palladium(0) bis(dibenzylideneacetone), Pd(dba)₂
• Linear Formula: (C₆H₅CH=CHCOCH=CHC₆H₅)₂Pd
• CAS Number: 32005-36-0
• Molecular Weight: 575.00
• MDL number: MFCD00051942
• UNSPSC Code: 12161600
• PubChem Substance ID: 24853668
• NACRES: NA.22

Properties

• form: powder
• Quality Level: 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
• 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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves