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328774 Sigma-Aldrich

Tris(dibenzylideneacetone)dipalladium(0)

97%

Synonym: Pd2dba3, Pd2(dba)3

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Properties

Related Categories Catalysis, Catalysis and Inorganic Chemistry, Chemical Synthesis, Development Quantities for Research, Homogeneous Pd Catalysts,
InChI Key   CYPYTURSJDMMMP-WVCUSYJESA-N
assay   97%
mp   152-155 °C (lit.)

Description

Packaging

1, 5, 25, 50, 100, 500 g in glass bottle

500 mg in glass bottle

Application

• Catalyst for Suzuki coupling of aryl chlorides (eq. 1)
• Catalyst for Heck coupling of aryl chlorides (eq. 2)
• Catalyst for arylation of ketones (eq. 3)
• Catalyst for Buchwald-Hartwig amination of aryl halides (eq. 4)
• Catalyst for fluorination of allylic chlorides (eq. 5)
• Catalyst for β-arylation of carboxylic esters (eq. 6)
• Catalyst for carbonylation of 1,1-dichloro-1-alkenes (eq. 7)
• Catalyst for conversion of aryl and vinyl triflates to aryl and vinyl halides (eq. 8)


Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Reactant involved in:
• Synthesis of nanosized palladium phosphides upon interaction with white phosphorous
• Preparation of palladium triphenylphosphine carbonyl cluster complexes
• Precursor for synthesis of functionalized multiwalled carbon nanotube-palladium complexes used as catalysts for Heck coupling reactions
• Selective carbon-sulfur bond formation via addition of S-S and S-H bonds to alkynes

Catalyst for:
• Suzuki cross-coupling reactions
• PCN- and PCS-pincer palladium complex catalyzed tandem allylation

General description

Tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) participates in the synthesis of azepane. Crystal structure of Pd2(dba)3 has been determined by three-dimensional X-ray data. Crystals of Pd2(dba)3 are reported to crystalize in triclinic system. It is widely used Pd(0) source in Pd-mediated transformations.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
2
Protocols & Articles

Articles

A Versatile Method for Suzuki Cross-Coupling Reactions of Nitrogen Heterocycles

In air, Pd(OAc)2 (9.1 mg, 1.141 mmol), PCy3 (22.4 mg, 1.181 mmol), and K3PO4�H2O (276 mg, 1.21 mmol) are added to a reaction vessel equipped with a stir bar. The vessel is sealed with a septum and pu...
Keywords: Chromatography, Column chromatography

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

BrettPhos Ligand Supported Palladium-Catalyzed C-O Bond Formation through an Electronic Pathway of Reductive Elimination: Fluoroalkoxylation of Activated Aryl Halides

A Pd/N-heterocyclic carbene-based catalyst achieves the Sonogashira coupling of an array of functionalized, ?-hydrogen-containing alkyl bromides and iodides under mild conditions. By furnishing the f...
Keywords: Chromatography, Cross couplings, Flash chromatography, Ligands, Sonogashira Coupling

C-O Cross-Coupling of Activated Aryl and Heteroaryl Halides with Aliphatic Alcohols-

We report an unprecedented BrettPhos ligand supported Pd-catalyzed C-O bond-forming reaction of activated aryl halides with primary fluoroalkyl alcohols. We demonstrate that the Phosphine ligand (Bre...
Keywords: Catalysis, Eliminations, Ligands, Reductive eliminations, Thin layer chromatography

Catalyst-Controlled Chemoselective Arylation of 2-Aminobenzimidazoles-

Pd2(dba)3/tris(tert-butyl)�HBF4/KF�2H2O serves as a mild, robust, and user-friendly method for the efficient Suzuki cross-coupling of a diverse array of aryl and heteroaryl halides with aryl- and het...
Keywords: Chromatography, Cross couplings, Flash chromatography

Catalysts and Metals

We supply a large variety of catalysts and metals that are of increasing importance to the synthetic organic chemist. This vast array of products is separated into two major categories: homogeneous a...
ChemFiles Volume 1 Article 3

Cross Coupling Reactions of Chiral Secondary Organoboronic Esters With Retention of Configuration-

We describe a systematic study of the scope and relationship between ligand structure and activity for a highly efficient and selective class of catalysts containing sterically hindered chelating alk...
Keywords: Aminations, Gas chromatography, Ligands

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

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

Palladium/Tris(tert-butyl)phosphine-Catalyzed Suzuki Cross- Couplings in the Presence of Water

The Suzuki reaction is an exceptionally useful cross-coupling process that has been widely applied in synthetic chemistry, and boronic acids are, by far, the most commonly employed coupling partner. ...
Keywords: Chromatography, Column chromatography, Cross couplings, Eliminations, Oxidative additions, Suzuki reactions

The First Negishi Cross-Coupling Reaction of Two Alkyl Centers Utilizing a Pd-N-Heterocyclic Carbene (NHC) Catalyst

The development of an NHC-based system capable of cross-coupling sp3-sp3 centers in high yield has been a long-standing challenge. This communication describes the use of a Pd-NHC catalytic system th...
Keywords: Catalysis, Chromatography, Cross couplings, Flash chromatography

Transition-Metal Catalysts

A variety of transition-metal catalysts for the Suzuki coupling reaction are now available in our catalog. The majority of these catalysts are palladium- and nickelbased, typically utilizing phosphin...
ChemFiles Volume 1 Article 1
Keywords: Coupling reactions, Ligands, Suzuki coupling

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

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