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| | Bis(dibenzylideneacetone)palladium Basic information | | Reaction |
| | 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) |
| | Bis(dibenzylideneacetone)palladium Usage And Synthesis |
| Reaction |
- Palladium-catalyzed acylation of unsaturated halides by anions of enol ethers.
- Asymmmetric Allylation reactions.
- Intramolecular reactions with alkenes.
- Carbonylation reactions.
- 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 |
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