Tris(4-methoxyphenyl)phosphine

Chemical Properties

White to pale yellow crystalline powder

Uses

suzuki reaction

Uses

Tris(4-methoxyphenyl)phosphine is a useful intermediate employed in organic synthesis and in other chemical processes.

Application

Tris(4-methoxyphenyl)phosphine is used as a ligand in organometallic chemistry and homogeneous catalysis.
This compound is suitable for the following reaction types: Buchwald-Hartwig Cross Coupling Reaction, Heck Reaction, Hiyama Coupling, Negishi Coupling, Sonogashira Coupling, Stille Coupling, Suzuki-Miyaura Coupling, and Cross Couplings.

Synthesis

To a solution of tertiary phosphine oxides 2 (0.4mmol) in CH2Cl2 (2mL) was added oxalyl chloride (0.4mmol) dropwise at room temperature under an argon atmosphere. After 30 minutes, HEH (1mmol) was added to the mixture in one portion, and TEA (3mmol) was added. The mixture was stirred for another 2h at 40°C and then diluted with H2O (10mL). The resulting mixture was extracted with CH2Cl2 repeatedly. The extracts were dried (anhydrous Na2SO4) and evaporated. The crude product was purified by column chromatography on silica gel using ethyl acetate/petroleum ether to afford the pure product Tris(4-methoxyphenyl)phosphine.