Tris(dibenzylideneacetone)dipalladium(0)
| Tris(dibenzylideneacetone)dipalladium(0) | ||
|---|---|---|
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dipalladium(0)-3D-balls.png) | ||
| IUPAC name Tris(dibenzylideneacetone)dipalladium | ||
| Other names Pd2(dba)3 | ||
| Identifiers | ||
| CAS number | 51364-51-3  | |
| Properties | ||
| Molecular formula | C51H42O3Pd2 | |
| Molar mass | 915.72 g mol−1 | |
| Melting point | 152 -155 °C | |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | ||
| 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
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
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
- ↑ 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.
- ↑ Jiro Tsuji and Ian J. S. Fairlamb "Tris(dibenzylideneacetone)dipalladium–Chloroform" E-EROS, 2008. doi:10.1002/047084289X.rt400.pub2
- ↑ 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.
- ↑ Hartwig, J. F. (2010). Organotransition Metal Chemistry, from Bonding to Catalysis. New York: University Science Books. ISBN 1-891389-53-X.
- ↑ 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
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