2013/04/22 by John R. Stille, F. Christopher Pigge, Christopher S. Regens +3 · 1 citation
Chemistry · #Catalytic Cross-Coupling Reactions #Catalytic C–H Functionalization Methods #Asymmetric Synthesis and Catalysis
paper · doi:10.1002/047084289x.rb138.pub3
openalex publication_date 2013/04/22 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/29
[32005-36-0] C34H28O2Pd (MW 575.01) InChI = 1S/2C17H14O.Pd/c2*18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;/h2*1-14H;/b2*13-11+,14-12+; InChIKey = UKSZBOKPHAQOMP-SVLSSHOZSA-N (catalyst for allylation of stabilized anions,1 cross coupling of allyl, alkenyl, and aryl halides with organostannanes,2 cross coupling of vinyl halides with alkenyl zinc species,3 cyclization reactions,4 and carbonylation of alkenyl and aryl halides,5 air stable Pd0 complex used as a homogeneous Pd0-precatalyst in the presence of additional external ligands) Alternative Name: palladium(0) bis(dibenzylideneacetone). Physical Data: mp 135 °C (dec). Solubility: insoluble in H2O, soluble in organic solvents (dichloromethane, chloroform, 1,2-dichloroethane, acetone, acetonitrile, benzene, and others) Form Supplied In: black solid; commercially available. Preparative Method: prepared by the addition of sodium acetate to a hot methanolic solution of dibenzylideneacetone (dba) and Na2[Pd2Cl6] (from Palladium(II) Chloride and NaCl), cooling, filtering, washing with MeOH, and air drying, gives Pd(dba)2; which is formulated more correctly as [Pd2(dba)3]dba.6, 12a Alternatively, palladium(II) chloride, sodium acetate, and dba can be added to a 40 °C methanolic solution, cooled, filtered, and washed copiously with H2O and acetone, in succession, and dried in vacuo.112a Handling, Storage, and Precautions: moderately air stable in the solid state; slowly decomposes in solution to metallic palladium and dibenzylideneacetone. Tris(dibenzylideneacetone)dipalladium(0)-Chloroform [52522-40-4] C52H43Cl3O3Pd2 (MW 1035.14) InChI = 1/3C17H14O.CHCl3.2Pd/c3*18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;2-1(3)4;;/h3*1-14H;1H;;/b3*13-11+,14-12+;;; InChIKey = LNAMMBFJMYMQTO-FNEBRGMMBW Alternative Name: dipalladium-tris(dibenzylideneacetone)chloroform complex. Physical Data: mp 131–135 °C,111 122–124 °C (dec).6, 112 Solubility: insoluble in H2O; soluble in chloroform, dichloromethane, and benzene. Form Supplied in: purple solid; commercially available. Preparative Method: the reaction of Na2[Pd2Cl6] and dba give Bis(dibenzylideneacetone)palladium(0), [Pd(dba)2dba], recrystallization from chloroform displaces the uncoordinated dba with chloroform to gives the title reagent as deep purple needles.112a Tris(dibenzylideneacetone)dipalladium [51364-51-3] C51H42O3Pd2 (MW 915.72) InChI = 1/3C17H14O.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+;; InChIKey = CYPYTURSJDMMP-WVCUSYJEBM Alternative Name: dipalladium-tris(dibenzylideneacetone). Physical Data: mp 152–155 °C.6a Form Supplied in: dark purple to black solid; commercially available. Preparative Method: prepared from dba and sodium tetrachloropalladate.6a