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578940

Sigma-Aldrich

Tri-tert-butylphosphonium tetrafluoroborate

97%

Synonym(s):

TTBP · HBF4, [(t-Bu)3PH]BF4

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About This Item

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

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.

Storage Class Code

11 - Combustible Solids

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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