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578940

Sigma-Aldrich

Tri-tert-butylphosphonium tetrafluoroborate

97%

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Synonym(s):
TTBP · HBF4, [(t-Bu)3PH]BF4
Linear Formula:
[[(CH3)3C]3PH]BF4
CAS Number:
131274-22-1
Molecular Weight:
290.13
MDL number:
MFCD04039975
UNSPSC Code:
12352101
PubChem Substance ID:
24880961
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Addition Reactions
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: Carbonylations
reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Sonogashira Coupling
reagent type: ligand
reaction type: Stille Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

mp

261 °C (lit.)

functional group

phosphine

SMILES string

F[B-](F)(F)F.CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C

InChI

1S/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

InChI key

YTJUCJAUJCXFTN-UHFFFAOYSA-O

Application

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Heck coupling with nonactivated alkenyl tosylates and phosphates: examples of effective 1,2-migrations of the alkenyl palladium(II) intermediates.
Anders L Hansen et al.
Angewandte Chemie (International ed. in English), 45(20), 3349-3353 (2006-04-12)
Synlett, 3001-3001 (2006)
Kevin R Campos et al.
Journal of the American Chemical Society, 128(11), 3538-3539 (2006-03-16)
This communication discloses the first instance of the enantioselective Pd-catalyzed alpha-arylation of N-Boc-pyrrolidine. The methodology relies on Beak's sparteine-mediated, enantioselective deprotonation of N-Boc-pyrrolidine to form the 2-pyrrolidinolithium specices in high enantiomeric ratio (er). Transmetalation of this intermediate with zinc chloride

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