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902284

TyrannoPhos

powder or crystals

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

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

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

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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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

Global Trade Item Number

SKUGTIN
902284-250MG04061838635792
902284-1G04061838635778