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Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C 6 H 5) 3 and often abbreviated to P Ph 3 or Ph 3 P. It is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic chemistry.
Triphenylphosphite is a notable example of polyamorphism in organic compounds, namely it exists in two different amorphous forms at temperatures about 200 K. [5] One polymorphic modification of triphenyl phosphite was obtained by means of crystallization in ionic liquids.
One of the first applications of phosphine ligands in catalysis was the use of triphenylphosphine in "Reppe" chemistry (1948), which included reactions of alkynes, carbon monoxide, and alcohols. [16] In his studies, Reppe discovered that this reaction more efficiently produced acrylic esters using NiBr 2 (PPh 3) 2 as a catalyst instead of NiBr 2.
In coordination chemistry, a ligand [a] is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's electron pairs , often through Lewis bases . [ 1 ]
Ph 3 PO is structurally related to POCl 3. [2] As established by X-ray crystallography, the geometry around P is tetrahedral, and the P-O distance is 1.48 Å. [3] Other modifications of Ph 3 PO have been found: For example, a monoclinic form crystalizes in the space group P2 1 /c with Z = 4 and a = 15.066(1) Å, b = 9.037(2) Å, c = 11.296(3) Å, and β = 98.47(1)°.The orthorhombic ...
The four phosphorus atoms are at the corners of a tetrahedron surrounding the palladium(0) center. This structure is typical for four-coordinate 18 e − complexes. [2] The corresponding complexes Ni(PPh 3) 4 and Pt(PPh 3) 4 are also well known.
Bis(triphenylphosphine)palladium chloride, PdCl 2 (PPh 3) 2. Coordination compounds of palladium contain ligands coordinated to a central Pd 0 or Pd 2+ center. They are typically synthesized by adding ligands to an ionic palladium compound.
Ligand-modified versions of Stryker's reagent have been reported. By changing the ligand to, e.g., P(O-iPr) 3 the selectivity can be improved significantly. [ 8 ] In addition, Lipshutz et al., have shown that the addition of a bidentate, achiral bis-phosphine ligand on the Cu center can lead to substrate-to-ligand ratios typically on the order ...