tricyclohexylphosphine

Tricyclohexylphosphine is an organophosphorus compound with the chemical formula P(C6H11)3. It is a tertiary phosphine and a member of the trialkylphosphine class of compounds. The molecule consists of a central phosphorus atom bonded to three cyclohexyl rings. Tricyclohexylphosphine is a white, crystalline solid at room temperature. It is known for its strong nucleophilicity and steric bulk, which are important properties that influence its reactivity and applications. It is generally soluble in organic solvents like tetrahydrofuran, dichloromethane, and hexane, but insoluble in water.

This compound finds significant use as a ligand in organometallic chemistry and catalysis. The bulky cyclohexyl groups create a sterically demanding environment around the phosphorus atom, which can influence the coordination geometry and electronic properties of metal complexes. This steric hindrance can also promote certain reaction pathways and enhance selectivity in catalytic processes. Tricyclohexylphosphine is particularly effective in palladium-catalyzed cross-coupling reactions, such as the Suzuki, Heck, and Buchwald-Hartwig amination reactions. Its ability to stabilize low-valent metal species and facilitate oxidative addition steps makes it a valuable tool for synthetic chemists. It is typically handled under an inert atmosphere due to its sensitivity to oxidation.