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| ImageFile1 = Pd2(dba)3.png<!--structure is not quite perfect with respect to cis vs trans-ness of the alkenes--> |
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|verifiedrevid = 429834506 |
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| ImageFile2 = Tris(dibenzylideneacetone)dipalladium(0)-3D-balls.png |
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| Name=Tris(dibenzylideneacetone){{shy}}dipalladium(0) |
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|ImageFile1 = Pd2(dba)3.png<!--structure is not quite perfect with respect to cis vs trans-ness of the alkenes--> |
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| IUPACName = Tris(dibenzylideneacetone)dipalladium |
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|ImageFile2 = Tris(dibenzylideneacetone)dipalladium(0)-3D-balls.png |
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| OtherNames = Pd<sub>2</sub>(dba)<sub>3</sub> |
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| ImageFile3 = File:Tris(dibenzylideneacetone)dipalladium(0).jpg |
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| Section1 = {{Chembox Identifiers |
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|IUPACName = Tris(dibenzylideneacetone)dipalladium |
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| CASNo =51364-51-3 |
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|OtherNames = Pd<sub>2</sub>(dba)<sub>3</sub> |
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|CASNo =51364-51-3 |
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| Section2 = {{Chembox Properties |
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|PubChem = 9811564 |
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| C = 51 | H = 42 | O = 3 | Pd = 2 |
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| MeltingPt = 152 -155 °C |
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'''Tris(dibenzylideneacetone)dipalladium(0)''' or Pd<sub>2</sub>(dba)<sub>3</sub> is an ] complex based on ] and ] used in ]. It was discovered in 1970.<ref>{{cite journal | last1 = Takahashi | first1 = Y. | last2 = Ito | first2 = Ts. | last3 = Sakai | first3 = S. | last4 = Ishii | first4 = Y. | title = A novel palladium(0) complex; bis(dibenzylideneacetone)palladium(0) | journal = Journal of the Chemical Society D: Chemical Communications | pages = 1065 | year = 1970 | doi = 10.1039/C29700001065 | issue = 17}}</ref> |
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|C=51 | H=42 | O=3 | Pd=2 |
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|MeltingPtC = 152 to 155 |
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'''Tris(dibenzylideneacetone)dipalladium(0)''' or is an ]. The compound is a complex of ](0) with ] (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 ] in ].<ref name=Tsuji/> |
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==Preparation and structure== |
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==Preparation and structure== |
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First reported in 1970,<ref>{{cite journal | last1 = Takahashi | first1 = Y. | last2 = Ito | first2 = Ts. | last3 = Sakai | first3 = S. | last4 = Ishii | first4 = Y. | title = A novel palladium(0) complex; bis(dibenzylideneacetone)palladium(0) | journal = Journal of the Chemical Society D: Chemical Communications | pages = 1065 | year = 1970 | doi = 10.1039/C29700001065 | issue = 17}}</ref> it is prepared from ] and ]. Because it is commonly recrystallized from ], the complex is often supplied as the adduct .<ref name=Tsuji>Jiro Tsuji and Ian J. S. Fairlamb "Tris(dibenzylideneacetone)dipalladium–Chloroform" E-EROS, 2008. {{doi|10.1002/047084289X.rt400.pub2}}</ref> The purity of samples can be variable.<ref>Zalesskiy, S. S., Ananikov, V. P., "Pd<sub>2</sub>(dba)<sub>3</sub> as a Precursor of Soluble Metal Complexes and Nanoparticles: Determination of Palladium Active Species for Catalysis and Synthesis", Organometallics 2012, 31, 2302. {{doi|10.1021/om201217r}}</ref> |
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It is prepared from ] and ].<ref>''Encyclopedia of Reagents for Organic Synthesis'', L.A. Paquette, Ed.: J. Wiley and Sons: Sussex, England, '''1996'''</ref> The complex has a dark purple/brown color, and, because it is commonly recrystallized from chloroform, it is often supplied as the adduct Pd<sub>2</sub>(dba)<sub>3</sub>•CHCl<sub>3</sub>. |
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In Pd<sub>2</sub>(dba)<sub>3</sub>, the pair of Pd atoms are separated by 320 ] but are tied together by dba units.<ref>{{cite journal | last1 = Pierpont | first1 = Cortlandt G. | last2 = Mazza | first2 = Margaret C. | title = Crystal and molecular structure of tris(dibenzylideneacetone)dipalladium(0) | journal = ] | volume = 13 | pages = 1891 | year = 1974 | doi = 10.1021/ic50138a020 | issue = 8}}</ref> The Pd(0) centres are bound to the alkene parts of the dba ]s. |
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In , the pair of Pd atoms are separated by 320 ] but are tied together by dba units.<ref>{{cite journal | last1 = Pierpont | first1 = Cortlandt G. | last2 = Mazza | first2 = Margaret C. | title = Crystal and molecular structure of tris(dibenzylideneacetone)dipalladium(0) | journal = ] | volume = 13 | pages = 1891 | year = 1974 | doi = 10.1021/ic50138a020 | issue = 8}}</ref> The Pd(0) centres are bound to the alkene parts of the dba ]s. |
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==Applications== |
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==Applications== |
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Pd<sub>2</sub>(dba)<sub>3</sub> is used as a source of soluble Pd(0), particularly as a ] for various coupling reactions in which it undergoes ] to Pd(II). Examples of reactions using this reagent are the ], ], ], ], as well as ].<ref>{{cite book | last = Hartwig | first = J. F. | title = Organotransition Metal Chemistry, from Bonding to Catalysis | publisher = University Science Books | place = New York | year = 2010 | isbn = 189138953X}}</ref> A related Pd(0) complex is ]. |
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is used as a source of soluble Pd(0), in particular as a ] for various coupling reactions. Examples of reactions using this reagent are the ], ], ], and ], as well as ].<ref>{{cite book | last = Hartwig | first = J. F. | title = Organotransition Metal Chemistry, from Bonding to Catalysis | publisher = University Science Books | place = New York | year = 2010 | isbn = 978-1-891389-53-5}}</ref> |
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Related Pd(0) complexes are <ref>John R. Stille, F. Christopher Pigge, Christopher S. Regens, Ke Chen, Adrian Ortiz and Martin D. Eastgate "Bis(dibenzylideneacetone)palladium(0)" |
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E-eros. 2013. {{doi|10.1002/047084289X.rb138.pub3}}</ref> and ]. |
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==References== |
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==References== |
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{{Palladium compounds}} |
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