Product Name
Tris(dibenzylideneacetone)dipalladium(0), 98%, ≥22.7% (as Pd)
Molecular Formula
C51H42O3Pd2
Certificate of Analysis (COA)
Synonyms
Bistris(dibenzylideneacetone)palladium(0)
IUPAC Name
tris((1E,4E)-1,5-diphenylpenta-1,4-dien-3-one);bis(palladium)
InChI Key
CYPYTURSJDMMMP-WVCUSYJESA-N
SMILES
C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.Pd.Pd
Product Introduction
Tris(dibenzylideneacetone)dipalladium(0) (Pd₂(dba)₃, CAS No. 51364-51-3) is a widely used zero-valent palladium catalyst precursor in modern organic synthesis and transition metal catalysis.
Pd₂(dba)₃ provides a stable source of Pd(0), which can generate active palladium species during catalytic reactions. Due to its excellent solubility in organic solvents, thermal stability, and compatibility with various phosphine and nitrogen ligands, it has become an important catalyst precursor for cross-coupling reactions, C–C bond formation, C–N bond formation, and pharmaceutical intermediate synthesis.
This palladium complex is extensively used in Suzuki–Miyaura coupling, Heck reactions, Buchwald–Hartwig amination, carbonylation reactions, and advanced organic transformations.
Mechanism / Principle
Palladium(0) Catalyst Activation
Pd₂(dba)₃ functions as a Pd(0) reservoir that releases catalytically active palladium species.
Typical catalytic cycle:
- Pd₂(dba)₃ dissociates under reaction conditions.
- Active Pd(0) species coordinate with ligands to form catalytic intermediates.
- Oxidative addition occurs with organic electrophiles such as aryl halides.
- Transmetalation transfers organic groups from coupling partners.
- Reductive elimination forms new chemical bonds and regenerates the palladium catalytic cycle.
Key features:
- Stable Pd(0) source
- Excellent ligand compatibility
- Enables C–C and C–N coupling reactions
- Suitable for air-sensitive catalytic systems
Key Research Applications
1. Suzuki–Miyaura Cross-Coupling
Pd₂(dba)₃ is commonly used for palladium-catalyzed Suzuki coupling reactions.
Applications include:
- Biaryl synthesis
- Heteroaryl compound preparation
- Pharmaceutical intermediate synthesis
- Functional aromatic molecule construction
2. Heck Coupling Reaction
Pd₂(dba)₃ acts as a catalyst precursor in carbon–carbon coupling.
Applications include:
- Arylation of alkenes
- C–C bond formation
- Organic framework construction
- Fine chemical synthesis
3. Buchwald–Hartwig Amination
Used for palladium-catalyzed C–N bond formation.
Applications include:
- Aniline derivative synthesis
- Nitrogen-containing molecule preparation
- Pharmaceutical chemistry research
- Medicinal chemistry development
4. Pharmaceutical and Fine Chemical Synthesis
Pd₂(dba)₃ is an important catalyst in complex molecular synthesis.
Applications include:
- API intermediate synthesis
- Drug candidate preparation
- Synthetic route optimization
- Structure–activity relationship studies
5. Materials Chemistry
Palladium-catalyzed coupling reactions are essential in functional material development.
Applications include:
- Conjugated polymer synthesis
- Organic semiconductor materials
- π-conjugated molecule preparation
- Electronic material research
Advantages
- Efficient Pd(0) catalyst precursor
- High catalytic activity
- Broad substrate compatibility
- Compatible with various ligands
- Suitable for complex organic synthesis
- Widely used in pharmaceutical and materials research
Technical Notes
| Parameter |
Information |
| Catalyst Type |
Palladium(0) complex |
| Metal Center |
Pd(0) |
| Molecular Weight |
915.72 g/mol |
| Formula |
C₅₁H₄₂O₃Pd₂ |
| Main Use |
Cross-coupling catalyst |
| Typical Reactions |
Suzuki, Heck, Buchwald–Hartwig |
| Appearance |
Dark purple solid |
| Melting Point |
Approximately 152–155°C |
Note: Catalytic performance depends on substrate structure, ligand system, base, solvent, and reaction temperature.
Storage & Handling
- Store in a cool, dry place.
- Keep container tightly sealed.
- Protect from moisture and direct light.
- Store under inert atmosphere for long-term storage when possible.
- Avoid contact with strong oxidizing agents.
Pd₂(dba)₃ is commonly handled under nitrogen or argon conditions in sensitive catalytic reactions.
Research Areas
Researchers working in the following fields may benefit from Pd₂(dba)₃:
- Organic synthesis
- Transition metal catalysis
- Medicinal chemistry
- Pharmaceutical chemistry
- Organometallic chemistry
- Materials chemistry
- Fine chemical synthesis
Q1: What is Pd₂(dba)₃?
A: Pd₂(dba)₃ (CAS No. 51364-51-3) is a palladium(0) catalyst precursor widely used in cross-coupling and organic synthesis.
Q2: What is Pd₂(dba)₃ used for?
A: It is mainly used for:
- Suzuki coupling reactions
- Heck reactions
- C–N coupling reactions
- Pharmaceutical synthesis
Q3: Why is Pd₂(dba)₃ used as a palladium source?
A: It provides a stable Pd(0) source and can generate active catalytic species under reaction conditions.
Q4: Is Pd₂(dba)₃ a Pd(0) or Pd(II) compound?
A: Pd₂(dba)₃ contains palladium in the zero oxidation state (Pd(0)).
Q5: What is the difference between Pd₂(dba)₃ and Pd(dppf)Cl₂?
| Property |
Pd₂(dba)₃ |
Pd(dppf)Cl₂ |
| Metal State |
Pd(0) |
Pd(II) |
| Ligand |
Dibenzylideneacetone |
dppf phosphine |
| Main Role |
Pd(0) precursor |
Preformed Pd catalyst |
| Typical Use |
Broad cross-coupling |
Suzuki/C–C coupling |
Q6: Can Pd₂(dba)₃ be used for Suzuki coupling?
A: Yes. Pd₂(dba)₃ is widely used as a palladium source for Suzuki–Miyaura coupling reactions.
Q7: How should Pd₂(dba)₃ be stored?
A: Store sealed in a dry environment and minimize exposure to air and moisture.
Q8: What are common alternatives to Pd₂(dba)₃?
A: Common alternatives include:
- Pd(PPh₃)₄
- Pd(dppf)Cl₂
- Pd(OAc)₂
- Pd₂(dba)₃·CHCl₃
