Tris(dibenzylideneacetone)dipalladium(0)

Tris(dibenzylideneacetone)dipalladium(0) or [Pd₂(dba)₃] is an organopalladium compound. The compound is a complex of palladium(0) with dibenzylideneacetone (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.^[1]

Tris(dibenzylideneacetone)­dipalladium(0)

Names
IUPAC name Tris(dibenzylideneacetone)dipalladium
Other names Pd2(dba)3
Identifiers
CAS Number	51364-51-3 Y
3D model (JSmol)	Interactive image
ChemSpider	7987319
ECHA InfoCard	100.122.794
EC Number	610-654-4
PubChem CID	9811564
InChI InChI=1S/3C17H14O.2Pd/c3*18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;;/h3*1-14H;;/b3*13-11+,14-12+;; Key: CYPYTURSJDMMMP-WVCUSYJESA-N
SMILES C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C1=CC=C(C=C1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]
Properties
Chemical formula	C51H42O3Pd2
Molar mass	915.73 g·mol−1
Melting point	152 to 155 °C (306 to 311 °F; 425 to 428 K)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H317, H319, H335, H411
Precautionary statements	P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Preparation and structure

First reported in 1970,^[2] it 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].^[1] The purity of samples can be variable.^[3]

In [Pd₂(dba)₃], the pair of Pd atoms are separated by 320 pm but are tied together by dba units.^[4] The Pd(0) centres are bound to the alkene parts of the dba ligands.

Applications

[Pd₂(dba)₃] is used as a source of soluble Pd(0), in particular as a catalyst for various coupling reactions. Examples of reactions using this reagent are the Negishi coupling, Suzuki coupling, Carroll rearrangement, and Trost asymmetric allylic alkylation, as well as Buchwald–Hartwig amination.^[5]

Related Pd(0) complexes are [Pd(dba)₂]^[6] and tetrakis(triphenylphosphine)palladium(0).