Tris(dibenzylideneacetone)dipalladium(0) or Pd 2(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 Pd 2(dba) 3·CHCl 3. [2 ]
2(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 [3 ] ligands.
Applications [ edit ]
2(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 and [5 ] tetrakis(triphenylphosphine)palladium(0).
References [ edit ]
^ 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