131274-22-1 Usage
Description
Tri-tert-butylphosphine tetrafluoroborate is a white to light yellow crystalline powder that serves as a versatile ligand in various chemical reactions, particularly in palladium-catalyzed processes. It is known for its effectiveness in promoting enantioselectivity and facilitating cross-coupling reactions.
Uses
Used in Pharmaceutical Industry:
Tri-tert-butylphosphine tetrafluoroborate is used as a ligand for the palladium-catalyzed enantioselective α-arylation of N-boc-pyrrolidine, which is a crucial step in the synthesis of various pharmaceutical compounds.
Used in Chemical Synthesis:
Tri-tert-butylphosphine tetrafluoroborate is used as a hindered phosphine salt with a Pd(0)-15-membered, triolefinic, macrocycle in Suzuki cross-coupling reactions of aryl bromides and chlorides. This application aids in the formation of substituted biaryl compounds, which are essential in the synthesis of various organic molecules.
Used in Dye-Sensitized Solar Cells:
Tri-tert-butylphosphonium tetrafluoroborate is used in the synthesis of a novel organic dye with a fluorenone conjugation bridge, which is employed in dye-sensitized solar cells to improve their efficiency and performance.
Used in Heck Coupling Reactions:
Tri-tert-butylphosphine tetrafluoroborate is utilized in the Heck coupling of non-activated vinyl tosylates with electron-deficient olefins, contributing to the synthesis of complex organic molecules and materials.
Reaction
Air-stable, non-pyrophoric precursor of the Tri-t-butylphosphine ligand which is used in a variety of catalytic processes.
Ligand for Suzuki cross-couplings.
Ligand for Heck Reactions.
Ligand for Stille Cross-couplings.
Ligand for α-Arylation and vinylation of arylmandelic acid derivatives.
Ligand for direct arylation of hetercycles
Synthesis of benzocyclobutenes by C-H activation.
Cross-coupling of Grignard reagents and aryl bromides.
Palladium catalyzed annulation of haloanilines.
Palladium-Catalyzed Acylation.
Palladium Catalyzed Carbonylative Heck Reaction.
Palladium-catalyzed aminosulfonylation.
Palladium-catalyzed intramolecular C–O bond formation.
Ruthenium-catalyzed cross-coupling of aldehydes with arylboronic acid.
Check Digit Verification of cas no
The CAS Registry Mumber 131274-22-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,1,2,7 and 4 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 131274-22:
(8*1)+(7*3)+(6*1)+(5*2)+(4*7)+(3*4)+(2*2)+(1*2)=91
91 % 10 = 1
So 131274-22-1 is a valid CAS Registry Number.
InChI:InChI=1/C12H27P.BF4/c1-10(2,3)13(11(4,5)6)12(7,8)9;2-1(3,4)5/h1-9H3;/q;-1/p+1
131274-22-1Relevant articles and documents
Convenient preparation of tri-tert-butylphosphonium tetrafluoroborate
Saget, Tanguy,Cramer, Nicolai
, p. 2369 - 2371 (2011)
The versatile tri-tert-butylphosphonium tetrafluoroborate ligand is prepared in a convenient, simple, and high-yielding procedure without the isolation of sensitive intermediates. Georg Thieme Verlag Stuttgart New York.
Process for synthesizing tri-tert-butylphosphonium tetrafluoroborate
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Paragraph 0017; 0019-0020; 0022-0023; 0025-0026; ..., (2021/11/26)
A tert-butyl Grignard reagent is reacted with phosphorus trihalide and boron trifluoride, the reaction is finished, a hydrofluoric acid aqueous solution is added to form a salt, the layering is extracted, and the tri-tert-butylphosphonium - tetrafluoroborate is obtained through recrystallization. The method is simple, feasible, safe and environment-friendly. When the tert-butyl Grignard reagent is reacted with the phosphorus trihalide, the tert-butyl phosphorus intermediate acts in the reaction process by adding the boron trifluoride complex, thereby improving the halogen ion release property, improving the tri-substituted product to 94 - 95%, the reaction yield 85 - 87% and the organic solvent can be recycled.
γ-Selective cross-coupling of allylic silanolate salts with aromatic bromides using trialkylphosphonium tetrafluoroborate salts prepared directly from phosphine?borane adducts
Denmark, Scott E.,Werner, Nathan S.
supporting information; experimental part, p. 4596 - 4599 (2011/10/12)
The γ-selective, palladium-catalyzed cross-coupling of sodium (Z)-2-butenyldiethylsilanolate with a variety of aromatic bromides is reported. The protocol provides high yields (73-94%) and site selectivity (γ/α, 25:1 → > 99:1) in the coupling of electron-
