• USA Home
  • 222380 - Allylpalladium(II) chloride dimer

EMAIL THIS PAGE TO A FRIEND
222380 Sigma-Aldrich

Allylpalladium(II) chloride dimer

Green Alternative

98%

Synonym: [PdCl(C3H5)]2

  • CAS Number 12012-95-2

  • Empirical Formula (Hill Notation) C6H10Cl2Pd2

  • Molecular Weight 365.89

  •  Beilstein Registry Number 4124623

  •  EC Number 234-579-8

  •  MDL number MFCD00044874

  •  PubChem Substance ID 24853328

Purchase

Properties

Related Categories 12 Principles Aligned Products, C-H Activation, Catalysis, Catalysis and Inorganic Chemistry, Catalysts,
InChI Key   TWKVUTXHANJYGH-UHFFFAOYSA-L
assay   98%
greener alternative product characteristics   Catalysis
Learn more about the Principles of Green Chemistry.
storage temp.   2-8°C

Description

Packaging

1, 5 g in glass bottle

500 mg in glass bottle

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Allylpalladium(II) chloride dimer has been employed for the following studies:
• Synthesis of cationic palladium cataysts, used in the microwave-assisted Heck arylation.
• Synthesis of N-heterocyclic carbene-palladium-η3-allyl chloride complexes, which are efficient catalyst for the Suzuki-Miyaura cross-coupling of aryl bromides and activated aryl chlorides.
• Synthesis of 1,4-diallyl-1,2-dihydroisoquinolines.
• As catalyst for greener Buchwald-Hartwig coupling in TPGS-750-M.

On the Way Towards Greener Transition-Metal-Catalyzed Processes as Quantified by E Factors

General description

Allylpalladium(II) chloride dimer is employed as catalyst in Heck reaction. It also participates as catalyst in the tandem nucleophilic allylation-alkoxyallylation reaction of the alkynylaldehydes with allyl chloride and allyltributylstannane.

Sigma Life Science is committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for energy efficiency. Find details here.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
RT3510000
Protocols & Articles

Articles

A Bulky Biaryl Phosphine Ligand Allows for Palladium-Catalyzed Amidation of Five-Membered Heterocycles as Electrophiles

The palladium-catalyzed cascade reaction of 2-chloroaryl sulfonates with arylamine and amide nucleophiles provides direct access to�N-arylbenzimidazoles. This strategy selectively produces the hetero...
Keywords: Catalysis, Chromatography, Column chromatography, Mass spectrometry, Oxidative additions

A Single Phosphine Ligand Allows Palladium-Catalyzed Intermolecular C-O Bond Formation with Secondary and Primary Alcohols-

The substrate scope of the copper-free Sonogashira coupling has been successfully extended to cyclopropyl iodides, allowing an efficient access to a wide variety of functionalized alkynyl cyclopropan...
Keywords: Chromatography, Flash chromatography, Nuclear magnetic resonance spectroscopy, Purification, Sonogashira Coupling, Spectroscopy

Asymmetric Hydrosilylation

The asymmetric hydrosilylation of olefins has proven to be a useful method to access a variety of chiral alcohols.1 The introduction of the silica moiety allows further transformation of the molecule...
William Sommer
Aldrich ChemFiles 2008, 8.6, 4.
Keywords: Asymmetric synthesis, Chemfiles, Hydrosilylations, Ligands, transformation

Heck Reaction

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes, and aryl or vinyl halides (or triflates) to afford substituted alkenes.1,2 It is a useful carbon–carbon bond form...
Keywords: Asymmetric synthesis, Cancer, Catalysis, Coupling reactions, Cross couplings, Heck Reaction, Herbicides, Ligands, Organic synthesis, Solvents

Ligand-Controlled Palladium-Catalyzed Regiodivergent Suzuki- Miyaura Cross-Coupling of Allylboronates and Aryl Halides-

Pd-PEPPSI-IPent has proven to be an excellent catalyst for the Negishi cross-coupling reaction of secondary alkylzinc reagents with a wide variety of aryl/heteroaryl halides. Importantly, b-hydride e...
Keywords: Chromatography, Coupling reactions, Cross couplings, Eliminations, Flash chromatography, Ligands, Nuclear magnetic resonance spectroscopy, Purification

Palladium-Catalyzed Reduction of Allylic Esters

The palladium catalyzed reduction of allylic esters provides a convenient method to access chiral olefins.1Hayashi et al. studied the activity of the MOP ligand with palladium toward the reduction of...
William Sommer
Aldrich ChemFiles 2008, 8.6, 4.
Keywords: Catalysis, Chemfiles, Ligands, Reductions

The First Applications of Carbene Ligands in Cross-Couplings of Alkyl Electrophiles: Sonogashira Reactions of Unactivated Alkyl Bromides and Iodides

The synthesis of ?,?-alkynyl esters and amides using air-stable potassium alkynyltrifluoroborates as nucleophilic partners in a mild Suzuki-Miyaura cross-coupling reaction has been achieved. Propargy...
Keywords: Chromatography, Column chromatography, Coupling reactions, Cross couplings

The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides

A series of N-heterocyclic carbene catalysts (see picture) were prepared and evaluated in the Suzuki-Miyaura reaction. A variety of sterically encumbered tetra-ortho-substituted biaryl products were ...
Keywords: Chromatography, Flash chromatography

Protocols

Boxed reaction: Buchwald-Hartwig in Lipshutz Surfactant

Please consult the Safety Data Sheet for information regarding hazards and safe handling practices.
Keywords: Aminations, Buchwald-Hartwig amination, Chromatography, Flash chromatography, Ligands

Buchwald Hartwig Amination Kit

Please consult the Safety Data Sheet for information regarding hazards and safe handling practices.
Keywords: Chromatography, Column chromatography, Gas chromatography, High performance liquid chromatography, Ligands, Thin layer chromatography

Buchwald-Hartwig Amination Reaction in Water at Room Temperature using TPGS-750-M

TPGS-750-M, DL-α-Tocopherol methoxypolyethylene glycol succinate, is a designer surfactant composed of a lipophilic α-tocopherol moiety and a hydrophilic PEG-750-M chain, joined by an inexpensive suc...
Keywords: Aminations, Buchwald-Hartwig amination, Catalysis, Chromatography, Coupling reactions, Cross couplings, Environmental, Flash chromatography, Ligands

Procedures for Transition-Metal-Catalyzed Cross-Coupling Reactions

TPGS-750-M, DL-α-Tocopherol methoxypolyethylene glycol succinate, is a designer surfactant composed of a lipophilic α-tocopherol moiety and a hydrophilic PEG-750-M chain, joined by an inexpensive suc...
Keywords: Aminations, Buchwald-Hartwig amination, Catalysis, Chromatography, Coupling reactions, Cross couplings, Environmental, Evaporation, Flash chromatography, Heck Reaction, Ligands, Metathesis, Olefin metathesis

Related Content

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Palladium catalyzed cross-coupling reactions have revolutionized the way in which molecules are constructed. From the fields of organic synthesis and medicinal chemistry, to materials science and pol...
Keywords: Catalysis, Coupling reactions, Cross couplings, Materials Science, Medicinal chemistry, Organic synthesis, Polymer science, transformation

Peer-Reviewed Papers
15

References

Related Products

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?