Product Name
Tris(dibenzylideneacetone)dipalladium(0), 20% 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 organic synthesis and transition metal catalysis.
Pd₂(dba)₃ serves as a stable source of Pd(0), which can generate active palladium species under reaction conditions. It is extensively applied in carbon–carbon bond formation, cross-coupling reactions, and catalytic transformations, including Suzuki–Miyaura coupling, Heck reactions, Buchwald–Hartwig amination, and other palladium-catalyzed processes.
Due to its high catalytic efficiency, stability, and compatibility with various ligand systems, Pd₂(dba)₃ is an important catalyst for pharmaceutical synthesis, materials chemistry, and advanced organic transformation research.
Mechanism / Principle
Palladium(0) Catalyst Activation
Pd₂(dba)₃ functions as a palladium(0) precursor that releases catalytically active palladium species.
Catalytic process:
- Pd₂(dba)₃ dissociates under reaction conditions.
- Active Pd(0) species are generated through interaction with ligands or substrates.
- Pd(0) undergoes oxidative addition with organic electrophiles.
- Subsequent transmetalation and reductive elimination steps form new chemical bonds and regenerate the catalytic cycle.
Key features:
- Provides a stable Pd(0) source
- Enables efficient C–C and C–N bond formation
- Compatible with diverse ligand systems
- Supports mild catalytic reaction conditions
Key Research Applications
1. Suzuki–Miyaura Cross-Coupling
Pd₂(dba)₃ is widely used in palladium-catalyzed cross-coupling reactions.
Applications include:
- Aryl–aryl coupling
- Heteroaryl synthesis
- Pharmaceutical intermediate preparation
- Functional molecule synthesis
2. Heck Reaction
Pd₂(dba)₃ serves as a catalyst precursor for carbon–carbon coupling reactions.
Applications include:
- Olefin arylation
- C–C bond formation
- Fine chemical synthesis
- Organic functionalization
3. Buchwald–Hartwig Amination
Pd₂(dba)₃ is commonly used in palladium-catalyzed C–N bond formation.
Applications include:
- Amino compound synthesis
- Nitrogen-containing heterocycles
- Pharmaceutical molecule development
- Medicinal chemistry research
4. Pharmaceutical and Fine Chemical Synthesis
Pd₂(dba)₃ is an important catalyst in complex molecule construction.
Applications include:
- Drug intermediate synthesis
- Bioactive compound preparation
- Lead compound optimization
- Synthetic route development
5. Materials Chemistry and Polymer Research
Palladium-catalyzed coupling reactions are widely used in functional material synthesis.
Applications include:
- Organic semiconductor synthesis
- Conjugated polymer preparation
- Functional aromatic material development
- Electronic material research
Advantages
- Stable Pd(0) catalyst precursor
- High catalytic activity
- Broad reaction compatibility
- Suitable for cross-coupling chemistry
- Supports efficient C–C and C–N bond formation
- Widely used in pharmaceutical and materials synthesis
Technical Notes
| Parameter |
Information |
| Catalyst Type |
Palladium(0) complex |
| Main Function |
Pd(0) catalyst precursor |
| Typical Reactions |
Suzuki, Heck, Buchwald–Hartwig coupling |
| Catalyst Loading |
Depends on substrate and reaction system |
| Common Solvents |
Organic solvents such as toluene, THF, dioxane, DMF |
| Handling |
Perform under inert atmosphere when required |
Note: Pd₂(dba)₃ performance may vary depending on ligand selection, substrate structure, and reaction conditions.
Storage & Handling
- Store in a cool, dry place.
- Keep container tightly sealed.
- Protect from moisture and air exposure.
- Store under inert atmosphere for long-term stability when possible.
- Avoid contact with strong oxidizing agents.
Pd₂(dba)₃ is commonly handled under nitrogen or argon conditions in air-sensitive catalytic reactions.
Research Areas
Researchers working in the following fields may benefit from Pd₂(dba)₃:
- Organic synthesis
- Transition metal catalysis
- Pharmaceutical chemistry
- Medicinal chemistry
- Materials chemistry
- Polymer synthesis
- Chemical process development
Q1: What is Pd₂(dba)₃?
A: Pd₂(dba)₃ (CAS No. 51364-51-3) is a palladium(0) catalyst precursor widely used in organic synthesis and cross-coupling reactions.
Q2: What is Pd₂(dba)₃ used for?
A: It is mainly used for:
- Suzuki coupling
- Heck reactions
- Buchwald–Hartwig amination
- Palladium-catalyzed bond formation
Q3: Why is Pd₂(dba)₃ used as a palladium source?
A: Pd₂(dba)₃ provides a stable and soluble Pd(0) source that can generate active catalytic species during organic transformations.
Q4: What reactions can Pd₂(dba)₃ catalyze?
A: Common reactions include:
- C–C coupling reactions
- C–N coupling reactions
- Arylation reactions
- Cross-coupling transformations
Q5: What is the difference between Pd₂(dba)₃ and Pd(PPh₃)₄?
| Property |
Pd₂(dba)₃ |
Pd(PPh₃)₄ |
| Metal State |
Pd(0) |
Pd(0) |
| Ligand Type |
Dibenzylideneacetone |
Triphenylphosphine |
| Main Use |
Catalyst precursor |
Direct Pd catalyst |
| Stability |
High |
High |
Q6: Does Pd₂(dba)₃ require additional ligands?
A: In many catalytic systems, additional ligands are added to tune palladium activity and selectivity.
Q7: How should Pd₂(dba)₃ be stored?
A: Store sealed in a dry environment and minimize exposure to air and moisture.
Q8: Is Pd₂(dba)₃ suitable for pharmaceutical synthesis?
A: Yes. It is widely used in pharmaceutical and fine chemical synthesis for forming complex molecular structures.
