Tris(dibenzylideneacetone)dipalladium-chloroform adduct

Reaction

1. Used for Pd-catalyzed asymmetric arylation, vinylation, and Allenylation of tert-cyclobutanols via enantioselective C−C Bond cleavage.
2. Used for synthesis of chiral chromans through the Pd-catalyzed asymmetric allylic alkylation (AAA).
3. Catalyst for double N-arylation of primary amines to synthesize multisubstituted carbazoles from 2,2‘biphenylylene ditriflates.
4. Paladium catalyst for regioand enantioselective allylic alkylation of ketones through allyl enol carbonates.
5. Used for Pd-catalyzed enantioselective C-3 allylation of 3-substituted-1H-indoles using trialkylboranes.
6. Used for enantioselective construction of spirocyclic oxindolic cyclopentanes by Pd-catalyzed trimethylenemethane-[3+2]-cycloaddition.
7. Used for Pd-catalyzed insertion of α-diazoesters into vinyl halides to generate α,β-unsaturated γ-amino Esters.
8. Pd catalyst for decarboxylative asymmetric allylic alkylation of enol carbonates.
9. Palladium catalyst for asymmetric addition of oxindoles and allenes.
10. Catalyst for diastereoand enantioselective formal [3+2]-cycloaddition between substituted vinylcyclopropanes and electron-deficient olefins.
11. Used for Pd-catalyzed asymmetric decarboxylative cycloaddition of vinylethylene carbonates with Michael sacceptors.
12. Catalyst for enantioselective [6+4] cycloaddition of vinyl oxetanes with azadienes to access ten-membered heterocycles.

Chemical Properties

purple to black crystalline powder

Uses

suzuki reaction

Uses

Tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct is a catalyst that is used in the preparation of anticancer activity of amino vinylindoles via palladium catalyzed coupling of hydrazone, haloindoles and amines.

Application

Tris(dibenzylideneacetone)dipalladium-chloroform adduct (Pd2dba3·CHCl3) was used in the following studies:
To compose the catalytic system for the preparation of homoallylpalladium complexes.These complexes underwent in situ Stille type cross coupling with various vinyltin reagents to afford the cyclized products bearing allyl appendages.
As palladium source in the asymmetric transformations of 3,4-epoxy-1-butene.
As catalyst for the Heck cross-coupling reaction of iodobenzene with styrene.
As cyclization catalyst.
As catalyst for [2+2+2] cycloaddtion of didehydrotriphenylenes to the corresponding extended triphenylenes.
As catalyst for the carbonylation of b,b-imidoyl iodides to the corresponding imidate esters used, in turn, to prepare cyclic, quaternary amino acids.

General Description

Tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (Pd₂dba₃·CHCl₃) is reported to serve as effective precatalysts, or precursors to the active Pd(0) catalyst.

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

Biological Activity

N -myristoyltransferase-1 (NMT-1) inhibitor that prevents activation of MAPK, PI 3-K and STAT3 signaling pathways. Exhibits antiproliferative activity against melanoma cells in vitro and in vivo . Also used as a cyclization catalyst.

Synthesis

Tris(dibenzylideneacetone)dipalladium-chloroform adduct is typically prepared from palladium(II) chloride. Step 1: Preparation of LiPdCl solution: Stir palladium chloride, lithium chloride and ethanol overnight under nitrogen protection, then filter. Step 2: Preparation of Tris(dibenzylideneacetone)dipalladium-chloroform adduct: Under nitrogen atmosphere, combine dibenzylideneacetone, ethanol, CHCl and sodium acetate. Add LiPdCl solution at 50.6C53.2C. After maintaining the reaction for a period, cool and filter. The product was washed with water and ethanol, then treated with ethanol/CHCl. After filtration and drying, vacuum drying yielded the target product.