Tris(dibenzylideneacetone)dipalladium

Description

Tris(dibenzylideneacetone) dipalladium (Tris DBA) is used as catalyst for a wide variety of Pd catalyzed reactions including Suzuki coupling, Heck coupling, Negishi coupling, Carroll reaarangement, Trost asymmetric allylic alkylation, Buchwald-Hartwig amination of acryl halides, fluorination of allylic chlorides, arylation of ketones, carbonylation of 1,1-dichloro-1-alkenes, ?-arylation of carboxylic esters, and conversion of aryl and vinyl triflates to aryl and vinyl halides. It is also involved in the synthesis of azepane. Tris DBA is also a novel inhibitor of N-myristoyltransferase-1 with significant antitumor activity.

Uses

Tris(dibenzylideneacetone)dipalladium is used in the preparation of semiconducting polymers processed from nonchlorinated solvents into high performance thin film transistors. Also used in the synthesis of polymer bulk-heterojunction solar sells as a semiconductor.

Reactions

1. Catalyst precursor for conversion of aryl chlorides, triflates, and nonaflates to nitroaromatics.
2. Catalyst for the synthesis of epoxides.
3. Catalytic asymmetric allylic and homoallylic diamination of terminal olefins.
4. Site-selective benzylic sp3 palladium-catalyzed direct arylation.
5. Palladium-catalyzed one-pot synthesis of tricyclic indolines.
6. Active catalyst for the Suzuki-Miyaura coupling of 2-pyridyl nucleophiles.
7. Catalyst in combination with BINAP for the asymmetric Heck Arylation of olefins.
8. Precursor for palladium-catalyzed carbon-nitrigen bond formation.
9. Catalyst for α-arylation of ketones,
10. Cross-coupling of aryl halides with aryl boronic acids.

References

1. https://en.wikipedia.org/wiki/Tris(dibenzylideneacetone)dipalladium(0)
2. http://www.sigmaaldrich.com
3. https://www.alfa.com
4. https://pubchem.ncbi.nlm.nih.gov
5. S. S. Bhandarkar, J. Bromberg, C. Carrillo, P. Selvakumar, R. K. Sharma, B. N. Perry, B. Govindarajan, L. Fried, A. Sohn, K. Reddy and J. L. Arbiser, Tris (Dibenzylideneacetone) Dipalladium, a N-Myristoyltransferase-1 Inhibitor, Is Effective against Melanoma Growth In vitro and In vivo, Clinical Cancer Research, 2008, vol. 18, 5743-5748

Chemical Properties

dark purple solid

Chemical Properties

Tris(dibenzylideneacetone)dipalladium is a dark red to brown, purple or black solid that is soluble in benzene and tetrahydrofuran. This substance is sensitive to air and moisture and should be stored in an inert gas environment at a temperature below 15°C. It is recommended to use amber glass bottles or storage containers for storage.

Uses

suzuki reaction

Uses

A cycloaddition catalyst.

Uses

Tris(dibenzylideneacetone)dipalladium is used in the preparation of semiconducting polymers processed from nonchlorinated solvents into high performance thin film transistors. It is also used as a semiconductor in the synthesis of polymer bulk-heterojunction solar cells.

Preparation

First reported in 1970,Tris(dibenzylideneacetone)dipalladium(0)  is prepared from dibenzylideneacetone and sodium tetrachloropalladate. Because it is commonly recrystallized from chloroform, the complex is often supplied as the adduct [Pd2(dba)3·CHCl3].The purity of samples can be variable.

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.

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

Structure and conformation

In [Pd2(dba)3], the pair of Pd atoms are separated by 320 pm but are tied together by dba units.The Pd(0) centres are bound to the alkene parts of the dba ligands.