Tris(dibenzylideneacetone)dipalladium(0)

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Tris(dibenzylideneacetone)dipalladium(0)
Pd2(dba)3.png
Tris(dibenzylideneacetone)dipalladium(0)-3D-balls.png
Identifiers
CAS number 51364-51-3 YesY
Properties
Molecular formula C51H42O3Pd2
Molar mass 915.72 g mol−1
Melting point 152 -155 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Tris(dibenzylideneacetone)dipalladium(0) or Pd2(dba)3 is an organometallic complex based on palladium and dibenzylideneacetone used in organic chemistry. It was reported in 1970.[1]

Preparation and structure[edit]

It is prepared from dibenzylideneacetone and sodium tetrachloropalladate. The complex has a dark-purple/brown color, and, because it is commonly recrystallized from chloroform, it is often supplied as the adduct Pd2(dba)3·CHCl3.[2]

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

Applications[edit]

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.[4]

Related Pd(0) complexes are Pd(dba)2[5] and tetrakis(triphenylphosphine)palladium(0).

References[edit]

  1. ^ Takahashi, Y.; Ito, Ts.; Sakai, S.; Ishii, Y. (1970). "A novel palladium(0) complex; bis(dibenzylideneacetone)palladium(0)". Journal of the Chemical Society D: Chemical Communications (17): 1065. doi:10.1039/C29700001065. 
  2. ^ Jiro Tsuji and Ian J. S. Fairlamb "Tris(dibenzylideneacetone)dipalladium–Chloroform" E-EROS, 2008. doi:10.1002/047084289X.rt400.pub2
  3. ^ Pierpont, Cortlandt G.; Mazza, Margaret C. (1974). "Crystal and molecular structure of tris(dibenzylideneacetone)dipalladium(0)". Inorg. Chem. 13 (8): 1891. doi:10.1021/ic50138a020. 
  4. ^ Hartwig, J. F. (2010). Organotransition Metal Chemistry, from Bonding to Catalysis. New York: University Science Books. ISBN 1-891389-53-X. 
  5. ^ John R. Stille, F. Christopher Pigge, Christopher S. Regens, Ke Chen, Adrian Ortiz and Martin D. Eastgate "Bis(dibenzylideneacetone)palladium(0)" E-eros. 2013. doi:10.1002/047084289X.rb138.pub3