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Merck

913030

Sigma-Aldrich

trYPhos

Umicore

Synonym(s):

(CyYPhos)(Me)PtBu2, Tricyclohexyl(1-(di-tert-butylphosphanyl)ethylidene)phosphane

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About This Item

Empirical Formula (Hill Notation):
C28H54P2
CAS Number:
Molecular Weight:
452.68
UNSPSC Code:
12352001
NACRES:
NA.22

Pricing and availability is not currently available.

Quality Level

form

powder

reaction suitability

reagent type: ligand

mp

137-139 °C

functional group

phosphine

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This Item
S1141856105677
form

powder

form

solid

form

powder or crystals

form

solid

solubility

H2O: 1 m at 20 °C, clear, colorless to almost colorless

solubility

H2O: soluble 100 mg/mL, clear, colorless to light yellow

solubility

H2O: 0.1 g/mL, clear

solubility

water: 20 mg/mL

grade

for molecular biology

grade

for molecular biology

grade

-

grade

-

product line

BioUltra

product line

BioReagent

product line

-

product line

-

impurities

DNases, none detected

impurities

-

impurities

-

impurities

-

General description

trYPhos is an ylide-functionalized phosphine ligand developed in the lab of Prof. V. Gessner with demonstrated uses in Pd-catalyzed cross coupling reactions, including the arylation of ketones and arylation of amines. trYPhosis the strongest donor of the available YPhos ligands, and is suited towards the most challenging alpha-arylation reactions.

Application

The electron-rich and sterically demanding trYPhos ligand has been used in the gold(I)-catalyzed hydroamination of acetylene,[1] and has shown to be effective in a range of Buchwald-Hartwig amination reactions. The strong electron-donor strength and sterically demanding nature of the ligand has been shown to increase the rate of formation of the catalytically active mono-phosphine palladium species, often leading to decreased reaction times or allowing the use of lower reaction temperatures. trYPhos is the most strongest donor of the available YPhosligands and has been found to be effective alpha-arylation of aliphatic cyclic ketones.[2]

Learn more about ylide-functionalized phosphines (YPhos)

Features and Benefits

Advantages of the trYPhos ligand over less electron rich ligand sources include, increased substrate scope in Buchwald-Hartwig amination reactions,[3] including aryl chlorides,[2] the use of more mild reaction conditions and improved activity in in C-N and C-C cross coupling reactions.[4][5] The increased electron donor stregth of trYPhos has been shown to be effective in the challenging alpha-arylation of aliphatic ketones.[2]

Legal Information

Product of Umicore

This product, its manufacturing or use, is the subject of one or more issued or pending U.S. Patents (and foreign equivalents) owned or controlled by Umicore PMC. The purchase of this product from Umicore PMC through Sigma-Aldrich, its affiliates or their authorized distributors conveys to the buyer a limited, one-time, non-exclusive, non-transferable, non-assignable license. Buyer′s use of this product may infringe patents owned or controlled by third parties. It is the sole responsibility of buyer to ensure that its use of the product does not infringe the patent rights of third parties or exceed the scope of the license granted herein.

For any further information on product please refer to your local Umicore PMC contact at www.pmc.umicore.com.
Yphos is a trademark of Umicore AG & Co. KG

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Julian Löffler et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 29(28), e202300151-e202300151 (2023-03-08)
Ylide-functionalized phosphines (YPhos) have recently proven to be strongly donating ligands that enable high catalyst activities in gold(I)-mediated transformations. We now report on a calorimetric study dealing with the [Au(YPhos)Cl] system and assess YPhos-Au bond dissociation enthalpies (BDE). Comparison with
Xiao-Qiang Hu et al.
Organic letters, 21(18), 7558-7562 (2019-08-31)
Ylide-functionalized phosphine (YPhos) ligands allow the palladium-catalyzed α-arylation of alkyl ketones with aryl chlorides with record setting activity. Using a cyclohexyl-substituted YPhos ligand, a wide range of challenging ketone substrates was efficiently and selectively monoarylated under mild conditions. A newly
Ilja Rodstein et al.
Chemical science, 13(45), 13552-13562 (2022-12-13)
The use of well-defined palladium(ii) complexes as precatalysts for C-X cross-coupling reactions has improved the use of palladium catalysts in organic synthesis including large-scale processes. Whereas sophisticated Pd(ii) precursors have been developed in the past years to facilitate catalyst activation
Ilja Rodstein et al.
The Journal of organic chemistry, 85(22), 14674-14683 (2020-09-11)
Ylide-substituted phosphines have been shown to be excellent ligands for C-N coupling reactions under mild reaction conditions. Here we report studies on the impact of the steric demand of the substituent in the ylide-backbone on the catalytic activity. Two new
Zhiyong Hu et al.
Angewandte Chemie (International ed. in English), 60(12), 6778-6783 (2021-01-12)
The coupling of aryl chlorides with Reformatsky reagents is a desirable strategy for the construction of α-aryl esters but has so far been substantially limited in the substrate scope due to many challenges posed by various possible side reactions. This

Articles

Explore innovative palladium-catalyzed coupling reactions with ylide-substituted phosphines. Learn about their impressive capabilities, enabling milder conditions and access to aryl chlorides.

Explore innovative palladium-catalyzed coupling reactions with ylide-substituted phosphines. Learn about their impressive capabilities, enabling milder conditions and access to aryl chlorides.

Electron-rich ylide-substituted phosphine ligands allow for palladium catalyzed coupling reactions at mild reaction conditions. These YPhos ligands enable the conversion of aryl chlorides with short reaction times.

Explore innovative palladium-catalyzed coupling reactions with ylide-substituted phosphines. Learn about their impressive capabilities, enabling milder conditions and access to aryl chlorides.

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