913030
trYPhos™
Umicore
Sinónimos:
(CyYPhos)(Me)PtBu2, Tricyclohexyl(1-(di-tert-butylphosphanyl)ethylidene)phosphane
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About This Item
Fórmula empírica (notación de Hill):
C28H54P2
Número de CAS:
Peso molecular:
452.68
Código UNSPSC:
12352001
NACRES:
NA.22
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Nivel de calidad
formulario
powder
idoneidad de la reacción
reagent type: ligand
mp
137-139 °C
grupo funcional
phosphine
Categorías relacionadas
Descripción general
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. trYPhos™is the strongest donor of the available YPhos™ ligands, and is suited towards the most challenging alpha-arylation reactions.
Aplicación
The electron-rich and sterically demanding trYPhos™ ligand 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. trYPhos™ is the most strongest donor of the available YPhos™ligands and has been found to be effective alpha-arylation of aliphatic cyclic ketones.
Learn more about ylide-functionalized phosphines (YPhos)
Learn more about ylide-functionalized phosphines (YPhos)
Características y beneficios
Advantages of the trYPhos™ 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. The increased electron donor stregth of trYPhos™ has been shown to be effective in the challenging alpha-arylation of aliphatic ketones.
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.
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
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
Certificados de análisis (COA)
Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»
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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
Formation of exceptional monomeric YPhos-PdCl2 complexes with high activities in coupling reactions.
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
Artículos
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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