Tricyclohexyl phosphine

Description

Tricyclohexyl phosphine is the tertiary phosphine with the formula P( C 6H11) 3. Commonly used as a ligand in organometallic chemistry, it is often abbreviated to PCy 3, where Cy stands for cyclohexyl. It is characterized by both high basicity (pK a = 9.7) and a large ligand cone angle (170°). Tricyclohexyl-phosphine is more basic (and so a better c-donor) than tribu tyiphosphine, which in turn is more basic than triphenyl phosphIne.

Chemical Properties

clear colorless to pale yellow solution

Uses

Tricyclohexylphosphine is used as a ligand in organometallic chemistry. As a reagent, it is used for a range of metal-catalyzed organic transformations. Crabtree's catalyst is an organoiridium compound containing tricyclohexyl phosphine used for hydrogenation of mono-, di-, tri-, and tetra- substituted substrates and hydrogen transfer reactions. Grubbs?catalysts consists of transition metal ruthenium and tricylohexyl phosphine utilized in olefin metathesis in synthetic organic chemistry.

Uses

1. Tricyclohexyl Phosphine is a ligand catalyst used primarily in organometallic chemistry.
2. Ligand used in the Pd-catalyzed coupling of malononitrile with aryl halides.
3. suzuki reaction: Bulky phosphine ligand used with a Pd(0)-triolefinic macrocycle catalyst for Suzuki coupling of aryl bromides and chlorides.
4. This ligand is applied with Ni as a key intermediate in the formation of cylcopentane compounds.
5. As a reagent, Tricyclohexylphosphine is used for a range of metal-catalyzed organic transformations.
6. Crabtree's catalyst is an organoiridium compound containing tricyclohexyl phosphine used for hydrogenation of mono-, di-, tri-, and tetra- substituted substrates and hydrogen transfer reactions.
7. Grubbs' catalysts consists of transition metal ruthenium and tricylohexyl phosphine utilized in olefin metathesis in synthetic organic chemistry.

Purification Methods

It recrystallises from EtOH [Boert et al. J Am Chem Soc 109 7781 1987]. [Beilstein 16 IV 947.]