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902284

TyrannoPhos

powder or crystals

Sustainability features

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
MDL number:
MFCD32068357
UNSPSC Code:
12161600
NACRES:
NA.22
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Product Name

TyrannoPhos,

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

sustainability

Sustainability features

functional group

phosphine

greener alternative category

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

InChI

1S/C33H51P/c1-30(2,3)23-17-24(31(4,5)6)20-28(19-23)34(27-15-13-14-16-27)29-21-25(32(7,8)9)18-26(22-29)33(10,11)12/h17-22,27H,13-16H2,1-12H3

InChI key

IWPJBOKLLTVJMY-UHFFFAOYSA-N

General description

We are committed to providing greener alternatives that adhere to the 12 Principles of Green Chemistry. This chiral ligand provides a chiral ligand framework for metal-catalyzed asymmetric transformations, enabling high stereoselectivity while reducing stereoisomeric waste, thus aligns with Green Chemistry principle "Catalysis". Click here for more information.

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

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

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