Tris(dibenzylideneacetone)dipalladium(0) or d₂(dba)₃is an organopalladium compound. The compound is a complex of

palladium Palladium is a chemical element; it has symbol Pd and atomic number 46. It is a rare and lustrous silvery-white metal discovered in 1802 by the English chemist William Hyde Wollaston. He named it after the asteroid Pallas (formally 2 Pallas), ...

(0) with

dibenzylideneacetone Dibenzylideneacetone or dibenzalacetone, often abbreviated dba, is an organic compound with the formula C17H14O. It is a pale-yellow solid insoluble in water, but soluble in ethanol. It was first prepared in 1881 by the German chemist Rainer Ludwi ...

(dba). It is a dark-purple/brown solid, which is modestly soluble in organic solvents. Because the dba ligands are easily displaced, the complex is used as a homogeneous catalyst in

organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...

Preparation and structure

First reported in 1970, it is prepared from

and

sodium tetrachloropalladate Sodium tetrachloropalladate is an inorganic compound with the chemical formula Na2PdCl4. This salt, and the analogous alkali metal salts of the form M2PdCl4, may be prepared simply by reacting palladium(II) chloride with the appropriate alkali me ...

. Because it is commonly recrystallized from

chloroform Chloroform, or trichloromethane (often abbreviated as TCM), is an organochloride with the formula and a common solvent. It is a volatile, colorless, sweet-smelling, dense liquid produced on a large scale as a precursor to refrigerants and po ...

, the complex is often supplied as the adduct d₂(dba)₃·CHCl₃Jiro Tsuji and Ian J. S. Fairlamb "Tris(dibenzylideneacetone)dipalladium–Chloroform" E-EROS, 2008. The purity of samples can be variable. In d₂(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

ligand In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's el ...

Applications

d₂(dba)₃is used as a source of soluble Pd(0), in particular as a

catalyst Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...

for various coupling reactions. Examples of reactions using this reagent are the

Negishi coupling The Negishi coupling is a widely employed transition metal catalyzed cross-coupling reaction. The reaction couples organic halides or triflates with organozinc compounds, forming carbon–carbon bonds (C–C) in the process. A palladium (0) s ...

, Suzuki coupling, Carroll rearrangement, and Trost asymmetric allylic alkylation, as well as Buchwald–Hartwig amination. Related Pd(0) complexes are d(dba)₂ref>John R. Stille, F. Christopher Pigge, Christopher S. Regens, Ke Chen, Adrian Ortiz and Martin D. Eastgate "Bis(dibenzylideneacetone)palladium(0)" E-eros. 2013. and

tetrakis(triphenylphosphine)palladium(0) Tetrakis(triphenylphosphine)palladium(0) (sometimes called quatrotriphenylphosphine palladium) is the chemical compound d(P(C6H5)3)4 often abbreviated Pd( PPh3)4, or rarely PdP4. It is a bright yellow crystalline solid that becomes brown upon d ...

References

{{Palladium compounds Catalysts Organopalladium compounds