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912042

Sigma-Aldrich

joYPhos™

Umicore

Sinónimos:

(CyYPhos)(Ph)PCy2, Tricyclohexyl((dicyclohexyl-phosphanyl)(phenyl)methylene)-phosphane

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About This Item

Fórmula empírica (notación de Hill):
C37H60P2
Número de CAS:
2271302-85-1
Peso molecular:
566.82
Número MDL:
MFCD34166196
Código UNSPSC:
12352001
NACRES:
NA.22

Nivel de calidad

100

Formulario

powder

idoneidad de la reacción

reagent type: ligand

mp

205-214 °C

grupo funcional

phosphine

cadena SMILES

[P](=C(P(C6CCCCC6)C5CCCCC5)c4ccccc4)(C3CCCCC3)(C2CCCCC2)C1CCCCC1

Clave InChI

IKSRBFVPKGZZND-UHFFFAOYSA-N

Descripción general

joYPhos™ 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.

Aplicación

The electron-rich and sterically demanding joYPhos™ ligand has been used in the gold(I)-catalyzed hydroamination of acetylene,citation 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 joYPhos™ 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.

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

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keYPhos™

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

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Certificados de análisis (COA)

Lot/Batch Number

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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
Sébastien Lapointe et al.
Accounts of chemical research, 55(5), 770-782 (2022-02-17)
The development of homogeneous catalysts is strongly connected to the design of new, sophisticated ligands, which resolve limitations of a given reaction protocol by manipulating the electronic properties of the metal and its spatial environment. Phosphines are a privileged class
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
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Artículos

Ylide Substituted Phosphines in Palladium Catalyzed Coupling

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

Ylide Substituted Phosphines in Palladium Catalyzed Coupling

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

Ylide-functionalized Phosphines (YPhos)

YPhos ligands enable efficient palladium-catalyzed coupling reactions under mild conditions, enhancing the synthesis of complex organic molecules.

Ylide Substituted Phosphines in Palladium Catalyzed Coupling

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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