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Thermo Scientific Chemicals
Tri-tert-butylphosphonium tetrafluoroborate, 97%
CAS: 131274-22-1 | C12H28BF4P | 290.13 g/mol
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Chemical Identifiers
CAS131274-22-1
IUPAC Nametetrafluoroboranuide; tri-tert-butylphosphanium
Molecular FormulaC12H28BF4P
InChI KeyYTJUCJAUJCXFTN-UHFFFAOYSA-O
SMILESF[B-](F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C
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Specifications
Specification Sheet
Specification SheetFormCrystals or powder or crystalline powder or chunks
Proton NMRConforms to structure
Appearance (Color)White
Assay from Supplier's CofA≥96.0% by Phosphorus NMR
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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.
Solubility
Soluble in methylene chloride and chloroform. Slightly soluble in terahydro furan. Insoluble in hexane, toluene and water.
Notes
Incompatible with strong oxidizing agents and halogens.
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.
Solubility
Soluble in methylene chloride and chloroform. Slightly soluble in terahydro furan. Insoluble in hexane, toluene and water.
Notes
Incompatible with strong oxidizing agents and halogens.
RUO – Research Use Only
General References:
- Convenient, air-stable replacement for tri-tert-butylphosphine, e.g. in Suzuki, Heck, Stille and Sonogashira coupling reactions: Org. Lett., 3, 4295 (2001).
- Takase, N.; Kuwabara, J.; Choi, S. J.; Yasuda, T.; Han, L.; Kanbara, T. Microwave-assisted polycondensation of 4-octylaniline with dibromoarylene. J. Polym. Sci., Part A: Polym. Chem. 2015, 53 (4), 536-542.
- He, Y.; Zhang, X.; Fan, X. Synthesis of diversely substituted 2-(furan-3-yl)acetates from allenols through cascade carbonylations. Chem. Commun. 2015, 51 (90), 16263-16266.