Synthesis
In a dry reaction flask, [Pd(allyl)Cl]₂ (1.91 g, 5.2 mmol) was dissolved in a dry acetonitrile solution (350 mL). Then, in a nitrogen-filled glove box, tri-tert-butylphosphine (6.54 g) was added to the palladium complex in one go. After stirring the reaction mixture for a period of time, a turbid yellow solution formed. Within a few minutes, the reaction mixture slowly became opaque. Stirring the reaction mixture for another 18 h yielded a milky white mixture. After the reaction was complete, the crude reaction mixture was filtered through a medium-sized filter, and the solid product was collected. The solid was washed with acetonitrile (3 × 50 mL) and dried under vacuum to obtain di(tri-tert-butylphosphine)palladium.
Figure 2. Synthetic Route of Bis(tri-tert-butylphosphine)palladium(0)
Reaction
- Introduced as an easier to handle Pd/P(t-Bu)3-based catalyst for the Negishi cross-coupling of aryl/vinyl chlorides.
- A versatile catalyst for the cross-coupling of aryl and vinyl chlorides.
- Catalyst for the amination of aryl chlorides and bromides using aqueous hydroxide bases.
- Useful catalyst for the cross-coupling of heteroaromatic carboxylic acids.
- Pd-catalyzed Newnan-Kwart rearrangement of O-aryl thiocarbamates.
- Cross-coupling of silanolates and halides.
- Elimination/isomerization of enol triflates derived from β-ketoesters.
Chemical Properties
Off white crystalline solid
Uses
Catalyst for Suzuki coupling on a multisubstituted sp 3 -carbon (eq. 1) Catalyst for Stille coupling reaction of aryl chlorides 2 (eq. 2) Catalyst for Negishi coupling reaction 3 (eq. 3) Catalyst for Heck coupling to form tetrasubstituted olefins 4 (eq. 4) Catalyst for Buchwald-Hartwig amination of aryl halide 5 (eq. 5) Catalyst for carbonylation of aryl halides with carbamoylsilanes 6 (eq. 6) t -Bu 3 P) 2 catalyst.
Uses
Bis(tri-tert-butylphosphine)palladium(0) is used in Coupling reactions, Heck couplings. It acts as a palladium catalyst for reductive carbonylation.
General Description
This product has been enhanced for catalytic efficiency.
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
