52522-40-4 Usage
Description
Tris(dibenzylideneacetone)dipalladium-chloroform adduct, also known as Pd2dba3·CHCl3, is a purple to black crystalline powder that serves as an effective precatalyst or precursor to the active Pd(0) catalyst. It is widely utilized in various chemical reactions, particularly in the field of organic synthesis.
Uses
1. Used in Suzuki Reaction:
Tris(dibenzylideneacetone)dipalladium-chloroform adduct is used as a catalyst in the Suzuki reaction for the formation of carbon-carbon bonds. The application reason is its ability to facilitate the cross-coupling of aryl or vinyl halides with aryl or vinyl boronic acids or esters, leading to the formation of biaryl and vinyl aryl compounds, which are essential in the synthesis of various pharmaceuticals, agrochemicals, and advanced materials.
2. Used in Anticancer Activity Preparation:
Tris(dibenzylideneacetone)dipalladium-chloroform adduct is used as a catalyst for the preparation of anticancer activity of amino vinylindoles via palladium-catalyzed coupling of hydrazone, haloindoles, and amines. The application reason is its effectiveness in promoting the formation of these biologically active compounds, which have potential applications in cancer treatment and therapy.
Reaction
Used for Pd-catalyzed asymmetric arylation, vinylation, and Allenylation of tert-cyclobutanols via enantioselective C?C Bond cleavage.
Used for synthesis of chiral chromans through the Pd-catalyzed asymmetric allylic alkylation (AAA).
Catalyst for double N-arylation of primary amines to synthesize multisubstituted carbazoles from 2,2‘biphenylylene ditriflates.
Paladium catalyst for regioand enantioselective allylic alkylation of ketones through allyl enol carbonates.
Used for Pd-catalyzed enantioselective C-3 allylation of 3-substituted-1H-indoles using trialkylboranes.
Used for enantioselective construction of spirocyclic oxindolic cyclopentanes by Pd-catalyzed trimethylenemethane-[3+2]-cycloaddition.
Used for Pd-catalyzed insertion of α-diazoesters into vinyl halides to generate α,β-unsaturated γ-amino Esters.
Pd catalyst for decarboxylative asymmetric allylic alkylation of enol carbonates.
Palladium catalyst for asymmetric addition of oxindoles and allenes.
Catalyst for diastereoand enantioselective formal [3+2]-cycloaddition between substituted vinylcyclopropanes and electron-deficient olefins.
Used for Pd-catalyzed asymmetric decarboxylative cycloaddition of vinylethylene carbonates with Michael sacceptors.
Catalyst for enantioselective [6+4] cycloaddition of vinyl oxetanes with azadienes to access ten-membered heterocycles.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 52522-40-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,2,5,2 and 2 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 52522-40:
(7*5)+(6*2)+(5*5)+(4*2)+(3*2)+(2*4)+(1*0)=94
94 % 10 = 4
So 52522-40-4 is a valid CAS Registry Number.
InChI:InChI=1/3C17H14O.CHCl3.2Pd/c3*18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;2-1(3)4;;/h3*1-14H;1H;;/b3*13-11+,14-12+;;;
52522-40-4Relevant articles and documents
Bis-chelated palladium(II) complexes with nitrogen-donor chelating ligands are efficient catalyst precursors for the CO/styrene copolymerization reaction
Milani, Barbara,Anzilutti, Anna,Vicentini, Lidia,O Santi, Andrea Sessanta,Zangrando, Ennio,Geremia, Silvano,Mestroni, Giovanni
, p. 5064 - 5075 (1997)
A series of dicationic bis-chelated palladium(II) complexes [Pd(N-N)2][X]2 (N-N = 2,2′-bipyridine (bipy), 1,10-phenanthroline (phen), and their substituted derivatives; X = PF6-, BF4-, OTf-, OTs-) has been synthesized and completely characterized both in the solid state and in solution. The synthetic procedure involves a simple one-pot reaction between Pd(MeCOO)2 and [(N-N)H][X]. These compounds are very active precatalysts for the CO/ styrene copolymerization yielding perfectly alternating polyketones. The crystal structures of some complexes of the series provide evidence that a distorsion from the ideal square planar geometry toward a twist conformation occurs. In DMSO solution, one of the two nitrogen-donor ligands is involved in a dissociative equilibrium yielding a monochelated complex with two cis coordination sites available for the copolymerization catalytic process. The catalytically active species is very stable in 2,2,2-trifluoroethanol, where its activity was found unaltered for at least 48 h of reaction without apparent decomposition to palladium metal. The addition of 1,4-benzoquinone (BQ) to the catalytic system has a strong influence on the yield and, above all, on the molecular weight of polyketones. The zerovalent palladium complexes [Pd(N-N)(BQ)], which might be formed during the copolymerization process, have been synthesized and characterized. The crystal structure of [Pd(bipy)(BQ)] shows that benzoquinone acts as a mono-olefinic ligand to Pd. In the presence of protons, the Pd(0) complexes are readily oxidized to Pd(II) with the reduction of benzoquinone to hydroquinone. When [(N-N)H][X] is used as the source of protons, the resulting Pd(II) species is the precatalyst and can immediately re-enter the catalytic cycle.
Catalytic C-phenylation of methyl acrylate with tetraphenylantimony(v) halides and carboxylates
Gushchin,Grunova,Moiseev,Morozov,Shavyrin,Dodonov
, p. 1376 - 1379 (2007/10/03)
Catalytic C-phenylation of methyl acrylate to methyl cinnamate with the Ph4SbX complexes (X = F, Cl, Br, OH, OAc, O2CEt) in the presence of the palladium compounds PdCl2, Pd(OAc)2, Pd2(dba)3, Pd(Ph3P)2Cl2, and Pd(dppf)Cl2 (dba is dibenzylideneacetone and dppf is bis(diphenylphosphinoferrocene)) was studied in organic solvents (MeCN, THF, DMF, MeOH, and AcOH). The highest yield of methyl cinnamate (73% based on the starting organometallic compound) was obtained for the Ph4SbCl- PdCl2 (1:0.04) system in acetonitrile.
