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Sigma-Aldrich

TyrannoPhos

Synonym(s):

Cyclopentylbis(3,5-di-tert-butylphenyl)phosphine, Phosphine ligand for nickel catalysis

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About This Item

Empirical Formula (Hill Notation):
C33H51P
CAS Number:
2097604-70-9
Molecular Weight:
478.73
UNSPSC Code:
12161600
NACRES:
NA.22

form

powder or crystals

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: catalyst
reaction type: Cross Couplings
reagent type: ligand

functional group

phosphine

SMILES string

CC(C1=CC(P(C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2)C3CCCC3)=CC(C(C)(C)C)=C1)(C)C

Application

This new aryl alkylphosphine ligand developed in Abby′s Doyle′s lab has been tailored specifically for nickel catalysis as demonstrated in the Suzuki coupling of acetals with boronic acids to generate benzylic ethers, reactions that pose challenges in Ni catalysis when using phosphine ligands developed for Pd-catalysed couplings.

Other Notes

Parameterization of phosphine ligands demonstrates enhacement of nickel catalysis via remote steric effects

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN3208

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Kevin Wu et al.
Nature chemistry, 9(8), 779-784 (2017-07-30)
The field of Ni-catalysed cross-coupling has seen rapid recent growth because of the low cost of Ni, its earth abundance, and its ability to promote unique cross-coupling reactions. Whereas advances in the related field of Pd-catalysed cross-coupling have been driven

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