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913294

Sigma-Aldrich

keYPhos™

Umicore

Sinónimos:

CyYPhos(Me)PCy2, Tricyclohexyl(1-(dicyclohexyl-phosphanyl)ethylidene)-phosphane

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About This Item

Fórmula empírica (notación de Hill):
C32H58P2
Número de CAS:
14185-94-5
Peso molecular:
504.75
Número MDL:
MFCD33021714
Código UNSPSC:
12352001
NACRES:
NA.22

Nombre del producto

keYPhos™,

Formulario

powder

Nivel de calidad

100

idoneidad de la reacción

reagent type: ligand

mp

167-169 °C

grupo funcional

phosphine

cadena SMILES

[P](=C(P(C5CCCCC5)C4CCCCC4)C)(C3CCCCC3)(C2CCCCC2)C1CCCCC1

InChI

1S/C32H58P2/c1-27(33(28-17-7-2-8-18-28)29-19-9-3-10-20-29)34(30-21-11-4-12-22-30,31-23-13-5-14-24-31)32-25-15-6-16-26-32/h28-32H,2-26H2,1H3

Clave InChI

TZVGFYHCFCNLKS-UHFFFAOYSA-N

Descripción general

keYPhos™is an ylide-functionalized phosphine ligand developed in the lab of Prof. V. Gessner at the Ruhr-University Bochum with demonstrated uses in Pd-catalyzed cross coupling reactions, including the arylation of ketones and arylation of amines. keYPhos™ is part of the YPhos™ family of ligands, also containing the joYPhos™ and trYPhos™ ligands.

Aplicación

The electron-rich and sterically demanding keYPhos™ has a methyl group in the ylide-backbone and is a valuable ligand for the palladium catalyzed coupling of aryl chlorides with primary and secondary alkyl and aryl amines at room temperature. keYPhos™has been used in the gold(I)-catalyzed hydroamination of acetylene, 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.

Learn more about ylide-functionalized phosphines (YPhos)

Características y beneficios

Advantages of the keYPhos™ligand over less electron rich ligand sources include, increased substrate scope in Buchwald-Hartwig amination reactions, including aryl chlorides, the use of more mild reaction conditions and improved activity in in C-N and C-C cross coupling reactions. keYPhos™ has been shown to perform well with common palladium sources such as Pd2(dba)3, Pd(OAc)2, [Pd(allyl)Cl]2 or [Pd(cinamyl)Cl]2.

Información legal

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

Producto relacionado

Referencia del producto
Descripción
Precios

913030

trYPhos™, Umicore

912042

joYPhos™, Umicore

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Jens Tappen et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 26(19), 4281-4288 (2020-01-24)
Palladium allyl, cinnamyl, and indenyl complexes with the ylide-substituted phosphines Cy3 P+ -C- (R)PCy2 (with R=Me (L1) or Ph (L2)) and Cy3 P+ -C- (Me)PtBu2 (L3) were prepared and applied as defined precatalysts in C-N coupling reactions. The complexes are
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.
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

Artículos

Ylide-functionalized Phosphines YPhos

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.

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