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912042

Sigma-Aldrich

joYPhos™

Umicore

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C37H60P2
Numéro CAS:
2271302-85-1
Poids moléculaire :
566.82
Code UNSPSC :
12352001
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Forme

powder

Pertinence de la réaction

reagent type: ligand

Pf

205-214 °C

Groupe fonctionnel

phosphine

Description générale

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.

Application

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)

Caractéristiques et avantages

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.

Informations légales

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

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

913030

trYPhos™, Umicore

913294

keYPhos™

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Certificats d'analyse (COA)

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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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Articles

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

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.

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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