Bis(dibenzylideneacetone)palladium

Base Information

• Chemical Name: Bis(dibenzylideneacetone)palladium
• CAS No.: 32005-36-0
• Molecular Formula: C34H28O2Pd
• Molecular Weight: 575.015
• Hs Code.: 28439000
• European Community (EC) Number: 608-691-6,620-687-6
• Mol file: 32005-36-0.mol

Synonyms:Bis(dibenzylideneacetone)palladium;32005-36-0;Bis(dibenzylideneacetone)palladium(0);PD(DBA)2;(1E,4E)-Bis(dibenzylideneacetone)palladium;TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(O);52409-22-0;MFCD00051942;190385-99-0;(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one;Palladium;C34H28O2Pd;bis(dibenzylideneactone)palladium;(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one,palladium;Palladium, bis((1,2,4,5-eta)-1,5-diphenyl-1,4-pentadien-3-one)-;C34-H28-O2-Pd;UKSZBOKPHAQOMP-SVLSSHOZSA-N;bis (dibenzylideneacetone)palladium;bis(dibenzylidene acetone)palladium;bis(dibenzylidene-acetone)palladium;bis(dibenzylideneacetone)-palladium;AMY39364;BCP22561;bis(dibenzilideneacetone)Palladium(0);AKOS015909150;bis (dibenzylideneacetone)palladium(0);bis(dibenzylidene acetone)palladium(0);bis(dibenzylideneacetone)-palladium(0);bis-(dibenzylideneacetone)palladium(0);AC-2607;GC10019;LS-0002;tris(dibenzylideneaceton)dipalladium(O);bis (dibenzylideneacetone)palladium (0);bis(dibenzylidene acetone)palladium (0);bis(dibenzylidene-acetone)palladium (0);bis(dibenzylideneacetone)-palladium (0);bis-(dibenzylideneacetone)palladium (0);tris(dibenzylidene-acetone)dipalladium(O);tris(dibenzylideneacetone) dipalladium(O);tris-(dibenzylideneacetone)dipalladium(O);tris (dibenzylideneacetone)dipalladium (O);tris(dibenzylideneacetone)-dipalladium (o);tris-(dibenzylideneacetone)dipalladium (O);BIS(DIBENZYLDENEACETONE)PALLADIUM(0);(1E,4E)-1,5-diphenyl-3-penta-1,4-dienone;H11614;A821096;J-400823;palladium;2-[(3-OXO-1,5-DIPHENYLPENTA-1,4-DIEN-2-YL)PALLADIO]-1,5-DIPHENYLPENTA-1,4-DIEN-3-ONE;BIS(DIBENZYLIDENEACETONE)PALLADIUM;BIS(DIBENZYLIDENEACETONE)PALLADIUM(0);PALLADIUM(0) BIS(DIBENZYLIDENEACETONE)

Chemical Property of Bis(dibenzylideneacetone)palladium

Chemical Property:

• Appearance/Colour: Purple powder
• Vapor Pressure: 1.25E-06mmHg at 25°C
• Melting Point: 150°C
• Boiling Point: 400.7oC at 760 mmHg
• Flash Point: 176.1oC
• PSA: 34.14000
• LogP: 7.96460
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Sensitive.: Air & Moisture Sensitive
• Solubility.: Chloroform (Slightly)
• Water Solubility.: insoluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 8
• Exact Mass: 574.11241
• Heavy Atom Count: 37
• Complexity: 272

Purity/Quality:

99% ^*data from raw suppliers

Bis(dibenzylideneacetone)palladium(TechnicalGrade) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 22-24/25-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CC(=O)C=CC2=CC=CC=C2.C1=CC=C(C=C1)C=CC(=O)C=CC2=CC=CC=C2.[Pd]
• Isomeric 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.[Pd]
• Uses: suzuki reaction 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. Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Technology Process of Bis(dibenzylideneacetone)palladium

There total 4 articles about Bis(dibenzylideneacetone)palladium which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

1,5-diphenyl-1,4-pentadiene-3-one (538-58-9) + palladium dichloride → bis(dibenzylideneacetone)-palladium(0) (32005-36-0)

Guidance literature:

palladium dichloride; With sodium chloride; In methanol; at 20 ℃; for 16h; Inert atmosphere; Schlenk technique;

1,5-diphenyl-1,4-pentadiene-3-one; In methanol; at 60 ℃; Inert atmosphere; Schlenk technique;

DOI:10.1002/ejoc.202100789

Reference yield: 95.4%

sodium tetrachloropalladate(II) + 1,5-diphenyl-1,4-pentadiene-3-one (538-58-9) → bis(dibenzylideneacetone)-palladium(0) (32005-36-0)

Guidance literature:

With sodium acetate; In methanol; at 57 ℃; Product distribution / selectivity; Inert atmosphere;

Reference yield:

sodium hexachlorodipalladate(II) + dibenzylideneacetone (35225-79-7) → bis(dibenzylideneacetone)-palladium(0) (32005-36-0)

Guidance literature:

sodium hexachlorodipalladate(II); dibenzylideneacetone; at 60 ℃; for 0.25h;

With sodium acetate; at 60 ℃; for 1h;

DOI:10.1002/chem.201704899

upstream raw materials:

1,5-diphenyl-1,4-pentadiene-3-one

dibenzylideneacetone

Downstream raw materials:

1,5-diphenyl-1,4-pentadiene-3-one

7-methyl-pyrido[2,3-b]pyrazine

di-μ-bromobis(N-methyl-3,4-dimethoxybenzalimine-6,C,N)dipalladium(II)

[(C₆H₂(OCH₃)2CHNCH₃Pd(P(C₆H₅)3)Br)]

Refernces

Matching the chirality of monodentate N-heterocyclic carbene ligands: A case study on well-defined palladium complexes for the asymmetric α-arylation of amides

10.1021/ol8021808

The research focuses on the development and application of chiral N-heterocyclic carbene (NHC) ligands derived from C2-symmetric diamines with naphthyl side chains for asymmetric catalysis. The purpose of the study was to synthesize well-defined palladium complexes with these NHC ligands and to investigate their performance in the asymmetric intramolecular γ-arylation of amides, aiming to obtain oxindoles with quaternary carbon centers in high yield and selectivity. The researchers prepared palladium complexes (NHC)Pd(cin)Cl and discovered that they exist as a mixture of diastereomers, which could be successfully separated and their absolute stereochemistry assigned. The study concluded that by correctly matching the chirality of the NHC complexes, high yields and selectivities could be achieved in the synthesis of chiral quaternary carbon centers. The chemicals used in the process included various NHC ligand precursors, palladium sources such as Pd(dba)2, Pd(OAc)2, and [Pd(cin)Cl]2, and a series of 2-bromoanilides as substrates for the asymmetric synthesis of oxindoles. The research demonstrated the significant impact of the ligand architecture on selectivity and identified the precatalyst [(Ra,Ra)-2a] as particularly effective, challenging the previous assumption that (Sa,Sa)-isomers were responsible for enantioselectivity in this subclass of chiral NHCs.

Palladium-Catalyzed Enantioselective Intramolecular Dearomative Heck Reaction

10.1021/jacs.8b09186

The study presents a protocol for synthesizing chiral spiroheterocyclic and benzofused heterocyclic compounds through a Pd-catalyzed enantioselective intramolecular dearomative Heck reaction. The reaction involves the cross-coupling of aryl halides or aryl triflates with the internal C=C bonds of indoles, benzofurans, pyrroles, and furans. The protocol utilizes various chiral phosphoramidite ligands, such as new BINOL- and H8-BINOL-based ligands, and (S)-SEGPHOS, which play crucial roles in achieving high enantioselectivities. The reactions are performed in the presence of palladium catalysts (Pd(OAc)? or Pd(dba)?) and bases like Cs?CO? or NEt?, with formic acid (HCO?H) often added to enhance enantioselectivity. The study demonstrates a broad substrate scope, yielding products with good to excellent yields and enantioselectivities. The synthesized compounds feature N/O-substituted quaternary carbon stereocenters and exocyclic olefin moieties, and further synthetic transformations of these products, such as hydrogenation, hydroboration, and ring-expanding rearrangements, are also explored without loss of enantiopurity.