Bis[1,2-bis(diphenylphosphino)ethane]palladium(0)

Synthesis

Under a nitrogen atmosphere, 0.2 g PdCl₂, 1.12 g Ph₂PCH₂CH₂PPh₂, and 12 ml dimethyl sulfoxide were mixed and heated to 140 °C to form a homogeneous solution, which was initially light red. The oil bath was removed, and the mixture was stirred vigorously for 30 min. Then, 0.3 ml (0.226 g) of hydrazine hydrate was slowly added dropwise. The reaction proceeded vigorously, and nitrogen gas was produced, turning the solution dark brown. The solution was cooled in a water bath, and brown crystals precipitated at approximately 125 °C. After slowly cooling to room temperature, the crystals were centrifuged, washed twice with 5 ml ethanol and twice with 5 ml diethyl ether, and dried under vacuum to obtain orange crystals, with a yield of approximately 78.2%.

Chemical Properties

yellow to orange crystalline powder

Uses

Bis[1,2-bis(diphenylphosphino)ethane]palladium(0) is a homogeneous catalyst most widely used in allylic substitution reactions; good catalyst for bulky substrates; slowly dissociating ligand that gives good stereoselectivity.

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: catalyst

storage

air and light sensitive. If stored under nitrogen or argon it is stable for  about one month. Avoid inhalation. Use in a fume hood.

Purification Methods

Bis[1,2-bis(diphenylphosphino)ethane]palladium(0) can be recrystallized from benzene-ethanol or ethanol.