328774

Tris(dibenzylideneacetone)dipalladium(0)

97%

• Synonym(s): Pd2dba3, Pd₂(dba)₃
• Linear Formula: (C₆H₅CH=CHCOCH=CHC₆H₅)₃Pd₂
• CAS Number: 51364-51-3
• Molecular Weight: 915.72
• MDL number: MFCD00013310
• UNSPSC Code: 12161600
• PubChem Substance ID: 24859746
• NACRES: NA.22

Properties

• Quality Level: 200
• Assay: 97%
• 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
• mp: 152-155 °C (lit.)
• SMILES string: [Pd].[Pd].O=C(\C=C\c1ccccc1)/C=C/c2ccccc2.O=C(\C=C\c3ccccc3)/C=C/c4ccccc4.O=C(\C=C\c5ccccc5)/C=C/c6ccccc6
• InChI: 1S/3C17H14O.2Pd/c3*18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;;/h3*1-14H;;/b3*13-11+,14-12+;;
• InChI key: CYPYTURSJDMMMP-WVCUSYJESA-N

Description

General description

Tris(dibenzylideneacetone)dipalladium(0) (Pd₂(dba)₃) is a versatile compound widely used as a Pd(0) source in various Pd-mediated transformations.[1] Pd₂(dba)₃ is known for its high reactivity and ability to facilitate oxidative addition reactions. It is prepared by reacting palladium salts with dibenzylideneacetone ligands. It acts as a catalyst for several reactions including Suzuki cross-coupling, Heck coupling, arylation, Buchwald-Hartwig amination, and fluorination. It is often used in catalytic amounts and has been shown to be effective in promoting coupling reactions between aryl halides and boronic acids.[2]

For small scale and high throughput uses, product is also available as ChemBeads (919772)

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Reactant involved in:


• Synthesis of azepanes[3]
• Synthesis of nanosized palladium phosphides upon interaction with white phosphorous
• Preparation of palladium triphenylphosphine carbonyl cluster complexes
• Precursor for synthesis of functionalized multiwalled carbon nanotube-palladium complexes used as catalysts for Heck coupling reactions
• Selective carbon-sulfur bond formation via addition of S-S and S-H bonds to alkynes

Catalyst for:


• Suzuki cross-coupling reactions
• PCN- and PCS-pincer palladium complex catalyzed tandem allylation
• Catalyst for Suzuki coupling of aryl chlorides[4] (eq. 1)
• Catalyst for Heck coupling of aryl chlorides[4] (eq. 2)
• Catalyst for arylation of ketones[5] (eq. 3)
• Catalyst for Buchwald-Hartwig amination of aryl halides[6] (eq. 4)
• Catalyst for fluorination of allylic chlorides[7] (eq. 5)
• Catalyst for β-arylation of carboxylic esters[8] (eq. 6)
• Catalyst for carbonylation of 1,1-dichloro-1-alkenes[9] (eq. 7)
• Catalyst for conversion of aryl and vinyl triflates to aryl and vinyl halides[10] (eq. 8)
• Pd source for enantioselective Tsuji Allylations[11][12]

Safety Information

• Pictograms: GHS07,GHS09
• Signal Word: Warning
• Hazard Statements: H317,H411
• Precautionary Statements: P261 - P272 - P273 - P280 - P302 + P352 - P333 + P313
• Hazard Classifications: Aquatic Chronic 2 - Skin Sens. 1
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves