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Tetrakis(triphenylphosphine)palladium(0), or Pd(PPh3)4, is perhaps the best-known catalyst for classical cross-coupling reactions. As evidenced by greater than 12,000 references in SciFinder, Pd(PPh3)4 is a workhorse of Pd(0)-catalyzed transformations and stands as the prototype upon which a diverse collection of palladium catalysts have been built.
Figure 1: The solid-state structure of tetrakis(triphenylphospine)palladium(0) (XRD).
In the solid state, Pd(PPh3)4 adopts a tetrahedral geometry1,, consistent with its 18-electron configuration (Figure 1). Though its homoleptic structure is relatively simple, the complex has been applied to an impressive variety of reactions. The most notable of these are cross-coupling reactions between aryl halides and transmetalating reagents, which were the subject of the 2010 Nobel Prize in Chemistry jointly awarded to Professors. Negishi2, Suzuki3, and Heck4 (Figure 2). In addition, the Sonogashira5 and Stille6 coupling reactions utilize Pd(PPh3)4 to facilitate transmetalation reactions between alkynes and tin reagents.
Figure 2: Examples of the three Nobel Prize-winning variations of Pd-catalyzed cross-coupling reactions.
Figure 3: Top: Examples of accepted (left) and rejected (right) Pd(PPh3)4.
Bottom: kilogram scale Tetrakis(triphenylphosphine)palladium(0), 99% (99.9+%-Pd) offered by Strem.
High quality pure Pd(PPh3)4 exhibits a beautiful golden-yellow color (Figure 3). Low quality or decomposed material however, often shows a dark orange-brown color or, in extreme cases of decay, a dark greenish color. This allows one to perform their own quality control: if it looks good, it is good! From milligrams to kilograms, Strem offers tetrakis-triphenylphosphine palladium(0) with consistently high quality, and the complex continues to be an invaluable part of any synthetic organic chemist’s toolbox.
Featured Product:
46-2150: Tetrakis(triphenylphosphine)palladium(0), 99% (99.9+%-Pd) (14221-01-3)
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References:
1. Zh. Strukt. Khim 1976, 17, 135. CCDC deposition number 1275987
2. J. Org. Chem. 2007, 72, 4246.
3. J. Am. Chem. Soc., 2009, 131, 5024.
4. J. Am. Chem. Soc. 1974, 96, 1133.
5. Tetrahedron Lett. 1965, 16: 4467–4470.
6. Chem. Lett., 1977, 6, 301-302.
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Hey all!
Does any one have a trick to removing Pd(PPh3)4 from a cross-coupling reaction? In my case I did a Negishi coupling.
VinylMgCl was cooled to 0C and THF soln of ZnBr2 is added and stirred for 15 min. My vinyl iodide was dissolved in THF and 0.03 eq Pd(PPh3)4 was added. The homogeneous soln was added to the organozinc reagent. Let stir at RT 2.5 hr.
Quench with 3 aliquots of sat. ammonium chloride and then add 1/2 aliquot of hexanes. Extract aqueous. Wash aqueous with ammonium chloride, water, brine, dry. NMR looks great except the Pd(PPh3)4.
The problem is the complex is soluable in hexane/THF so celite is a no go. Any help would be great. I know removing these types of catalysts can be a pain. I am trying to do a reaction on scale and a column is just not practical.
Thank you in advance!
Cheers!
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