Bis(triphenylphosphine)palladium(II) dichloride
Encyclopedia
Bispalladium(II) dichloride is a coordination compound of palladium
containing two triphenylphosphine
and two chloride
ligands. This yellow complex is often used for palladium-catalyzed coupling reactions
, e.g. the Sonogashira–Hagihara reaction. The complex is square planar. Both cis and trans isomers are known.
Commercially available, this compound may be prepared by reacting palladium(II) chloride
with triphenylphosphine:
The complex is an intermediate in the preparation of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4):
Palladium
Palladium is a chemical element with the chemical symbol Pd and an atomic number of 46. It is a rare and lustrous silvery-white metal discovered in 1803 by William Hyde Wollaston. He named it after the asteroid Pallas, which was itself named after the epithet of the Greek goddess Athena, acquired...
containing two triphenylphosphine
Triphenylphosphine
Triphenylphosphine is a common organophosphorus compound with the formula P3 - often abbreviated to PPh3 or Ph3P. It is widely used in the synthesis of organic and organometallic compounds. PPh3 exists as relatively air stable, colorless crystals at room temperature...
and two chloride
Chloride
The chloride ion is formed when the element chlorine, a halogen, picks up one electron to form an anion Cl−. The salts of hydrochloric acid HCl contain chloride ions and can also be called chlorides. The chloride ion, and its salts such as sodium chloride, are very soluble in water...
ligands. This yellow complex is often used for palladium-catalyzed coupling reactions
Palladium-catalyzed coupling reactions
Palladium compounds are used as a catalyst in many coupling reactions, usually as a homogeneous catalyst. Examples include:* Heck reaction between alkenes and aryl halides* Suzuki reaction between aryl halides and boronic acids...
, e.g. the Sonogashira–Hagihara reaction. The complex is square planar. Both cis and trans isomers are known.
Commercially available, this compound may be prepared by reacting palladium(II) chloride
Palladium(II) chloride
Palladium chloride, also known as palladium dichloride, are the chemical compounds with the formula PdCl2. PdCl2 is a common starting material in palladium chemistry – palladium-based catalysts are of particular value in organic synthesis. It is prepared by chlorination of...
with triphenylphosphine:
- PdCl2 + 2 PPh3 → PdCl2(PPh3)2
The complex is an intermediate in the preparation of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4):
- PdCl2(PPh3)2 + 2 PPh3 + 2.5 N2H4HydrazineHydrazine is an inorganic compound with the formula N2H4. It is a colourless flammable liquid with an ammonia-like odor. Hydrazine is highly toxic and dangerously unstable unless handled in solution. Approximately 260,000 tons are manufactured annually...
→ Pd(PPh3)4 + 0.5 N2 + 2 N2H5+Cl-