Tri-tert-butylphosphine tetrafluoroborate

Reaction

1. Air-stable, non-pyrophoric precursor of the Tri-t-butylphosphine ligand which is used in a variety of catalytic processes.
2. Ligand for Suzuki cross-couplings.
3. Ligand for Heck Reactions.
4. Ligand for Stille Cross-couplings.
5. Ligand for α-Arylation and vinylation of arylmandelic acid derivatives.
6. Ligand for direct arylation of hetercycles
7. Synthesis of benzocyclobutenes by C-H activation.
8. Cross-coupling of Grignard reagents and aryl bromides.
9. Palladium catalyzed annulation of haloanilines.
10. Palladium-Catalyzed Acylation.
11. Palladium Catalyzed Carbonylative Heck Reaction.
12. Palladium-catalyzed aminosulfonylation.
13. Palladium-catalyzed intramolecular C–O bond formation.
14. Ruthenium-catalyzed cross-coupling of aldehydes with arylboronic acid.

Chemical Properties

white to light yellow crystal powde

Uses

Tri-tert-butylphosphonium Tetrafluoroborate is used in the synthesis of substituted biaryl compounds via palladium catalyzed tandem Heck-direct arylation and tandem- sequential Heck-direct arylation-hydrogenation. Also used in the synthesis of a novel organic dye with fluorenone as conjugation bridge which is used in dye sensitized solar cells.

Uses

suzuki reaction
Hindered Phosphine salt employed with a Pd(0)-15-membered, triolefinic, macrocyle in Suzuki cross-coupling reactions of aryl bromides and chlorides. Also used in Heck coupling of non-activated vinyl tosylates with electron deficient olefins.
Ligand used in the Pd-catalyzed enantioselective α?arylation of N-boc-pyrrolidine.

Application

Tri-tert-butylphosphonium tetrafluoroborate is a ligand used in the palladium-catalyzed enantioselective alfa-arylation of N-boc-pyrrolidine. It is also used with a palladium(0)-15-membered, triolefinic, macrocyle in Suzuki cross-coupling reactions of aryl bromides and chlorides. Further, it is used in the Heck coupling of vinyl tosylates with olefins.

Preparation

Addition of HBF4 to a solution of tri-tert-butylphosphine in methylene chloride. Separation of the organic layer and removal of the solvent gives analytically pure Tri-tert-butylphosphine tetrafluoroborate.

storage

Tri-tert-butylphosphine tetrafluoroborate is indefinitely stable as a solid and in solution and requires no special handling. This compound is considered non-hazardous. Protection from oxygen is required in the presence of the base, as the highly air-sensitive tri-tert-butylphosphine will be formed.