Tri(2-furyl)phosphine

Reaction

1. Useful ligand for C-C coupling reactions.
2. Ligand used for the alkynylation of thioesters.
3. Ligand used for enol ester formation.
4. Ligand for palladium-catalyzed 3-Component coupling.
5. Ligand for palladium-catalyzed C-C coupling reaction.
6. Ligand for trans-olefin formation.
7. Olefin formation from N-tosylhydrazones and benzyl halides.
8. C-H arylation/alkenylation of 1-substituted tetrazoles. 

Chemical Properties

TRI(2-FURYL)PHOSPHINE is white to light yellow crystal powde

Uses

TRI(2-FURYL)PHOSPHINE is a phopshine ligand used in transition-metal mediated organic synthesis, in particular in wittig reactions to improved (Z) selectivity.

Uses

suzuki reaction

reaction suitability

reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: Cycloisomerizations
reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Oxidations
reagent type: ligand
reaction type: Sonogashira Coupling
reagent type: ligand
reaction type: Stille Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

Synthesis

The reaction flask was replaced with nitrogen atmosphere, under mechanical stirring, 20g of analytically pure furan, 34.8g of analytically pure TMEDA and 140mL of n-hexane were added into the reaction flask, 120mL of n-butyllithium (analytically pure) with a concentration of 2.5M/L was added dropwise at room temperature, after the dropwise addition was completed, the temperature was elevated to 50 and kept at 2h.

An analytically pure solution of 8g of n-hexane with a concentration of 3.5M/L of n-butyllithium (analytically pure) was added dropwise at 0 and kept at this temperature for 1h.

The reaction solution was poured into 200mL of saturated aqueous ammonium nitrate solution at 0, and stirred thoroughly, then the reaction solution was static stratified, and the organic phase was separated, and the aqueous phase was extracted with dichloromethane for 2-3 times, and the organic phase was combined, and the organic phase was concentrated to get the crude product, which was recrystallized with petroleum ether to get the crude product, and the crude product was extracted with petroleum ether to get the crude product, and the organic phase was concentrated to get the crude product. Recrystallized with petroleum ether, obtained white crystal product tris(2-furyl)phosphine 11.1g, the calculated yield was 82%, through the Agilent 1100 liquid chromatograph to get the product purity of 99.1%