478980-01-7

Basic information

• Product Name: ALLYLCHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)-4,5-DIHYDROIMIDAZOL-2-YLIDENE]PALLADIUM (II)
• Synonyms: ALLYLCHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)-4,5-DIHYDROIMIDAZOL-2-YLIDENE]PALLADIUM (II);Allylchloro[1,3-bis(2,6-di-i-propylphenyl)-4,5-dihydroimidazol-2-ylidene]palladium(II),97%;ALLYLCHLORO[1,3-BIS-(DIISOPROPYLPHENYL)-2-IMIDAZOLIDINYLIDENE]PALLADIUM(II);Allylchloro[1,3-bis(2,6-di-i-propylphenyl)4,5-dihydroimidazol-2-ylidene]palladium (II), 97%;Allyl[1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene]chloropalladium( II);Umicore CX23;UMicore CX23, 18% Pd, Product of UMicore;Allylchloro-[1,3-bis-(2,6-diisopropylphenyl)-2-imidazolidinylidene]palladium(II)
• CAS NO: 478980-01-7
• Molecular Formula: C₃₀H₄₃ClN₂Pd
• Molecular Weight: 573.55
• Product Categories: metal carbene complex;Pd
• Mol File: 478980-01-7.mol

Chemical Properties

• Melting Point: 206-210°C
• Appearance: white/Powder
• Storage Temp.: 2-8°C
• CAS DataBase Reference: ALLYLCHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)-4,5-DIHYDROIMIDAZOL-2-YLIDENE]PALLADIUM (II)(CAS DataBase Reference)
• NIST Chemistry Reference: ALLYLCHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)-4,5-DIHYDROIMIDAZOL-2-YLIDENE]PALLADIUM (II)(478980-01-7)
• EPA Substance Registry System: ALLYLCHLORO[1,3-BIS(2,6-DI-I-PROPYLPHENYL)-4,5-DIHYDROIMIDAZOL-2-YLIDENE]PALLADIUM (II)(478980-01-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 478980-01-7(Hazardous Substances Data)

Usage

Reaction

Catalyst for the cross-coupling of aryl chlorides or bromides with aromatic amines. Catalyst for the α-arylation of ketones. Catalyst for anaerobic alcohol oxidation.

Chemical Properties

Yellow crystal

Upstream product

• 258278-28-3 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene 
• 258278-25-0 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride 
• 777084-20-5 1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene hydrochloride 

Downstream Products

• 187737-37-7 propene 
• 67-64-1 acetone 

Relevant articles and documents

Activation and reactivity of (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes in cross-coupling reactions

The synthesis of mononuclear palladium-allyl complexes bearing one N-heterocyclic carbene (NHC) ligand was discussed. These complexes offered a straightforward entryway into a number of catalytic cycles by simple action of a base. The well-defined complexes were air- and moisture-stable. A single-crystal X-ray analysis was performed to confirm the structure of the family of complexes.

N-heterocyclic carbene–palladium complexes for Suzuki–Miyaura coupling reaction with benzyl chloride and aromatic boronic acid leading to diarylmethanes

A family of N-heterocyclic carbene–palladium(II)–N,N-dimethylbenzylamine complexes ((NHC)LPdCl2; L?=?N,N-dimethylbenzylamine) were synthesized as well as characterized using single-crystal X-ray diffraction and spectroscopic data. These complexes exhibited higher catalytic activities for the Suzuki reaction of benzyl chlorides to afford diarylmethanes under milder conditions than other efficient (NHC)LPdCl2 complexes. Using the optimum conditions, the expected coupling products were obtained in moderate to high yields. All reactions were carried out in air and all starting materials were used as supplied without purification.

PREPARATION OF DIPHENYL-BRIDGED SUBSTITUTED CYCLOPENTADIENYL-FLUORENYL LIGANDS

The present invention discloses efficient methods for preparing substituted cyclopentadienyl-fluorenyl catalyst components having a diphenyl bridge.

Development of a practical Buchwald-Hartwig amine arylation protocol using a conveniently prepared (NHC)Pd(R-allyl)Cl catalyst

Continuing efforts to establish a more general "user-friendly" protocol for the palladium-catalysed arylation of amines (Buchwald-Hartwig reaction) are described herein. Significant advances have been made through the use of the versatile (SIPr)Pd(methallyl)Cl complex in conjunction with the reliable base lithium hexamethyldisilazide (LHMDS). The Royal Society of Chemistry.

Synthetic and structural studies of (NHC)Pd(allyl)Cl complexes (NHC = N-heterocyclic carbene)

The synthesis and structural characterization of a series of palladium complexes bearing N-heterocyclic carbenes (NHC) as supporting ligands are described. The reaction of commercially available [Pd(allyl)Cl]2 and isolated or in situ generated NHC leads to monomeric palladium complexes where one NHC is bound to the metal center, as indicated by spectroscopic and single-crystal X-ray diffraction studies. The relative reactivity trend for these complexes as catalysts in aryl amination is discussed in terms of ligand steric properties, which vary as a function of imidazole-nitrogen substituents and perturbation resulting in modulation of ring planarity. The concept of buried volume is used to quantify the steric demand of each NHC in the corresponding complexes.