912042
joYPhos™
Umicore
Synonym(s):
(CyYPhos)(Ph)PCy2, Tricyclohexyl((dicyclohexyl-phosphanyl)(phenyl)methylene)-phosphane
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All Photos(3)
About This Item
Empirical Formula (Hill Notation):
C37H60P2
CAS Number:
Molecular Weight:
566.82
UNSPSC Code:
12352001
NACRES:
NA.22
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Quality Level
form
powder
reaction suitability
reagent type: ligand
mp
205-214 °C
functional group
phosphine
General description
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)
Learn more about ylide-functionalized phosphines (YPhos)
Features and Benefits
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.
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
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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Description
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Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Certificates of Analysis (COA)
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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
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
Thorsten Scherpf et al.
Angewandte Chemie (International ed. in English), 59(46), 20596-20603 (2020-07-30)
Organolithium compounds are amongst the most important organometallic reagents and frequently used in difficult metallation reactions. However, their direct use in the formation of C-C bonds is less established. Although remarkable advances in the coupling of aryllithium compounds have been
Thorsten Scherpf et al.
Angewandte Chemie (International ed. in English), 57(39), 12859-12864 (2018-06-05)
Phosphines are important ligands in homogenous catalysis and have been crucial for many advances, such as in cross-coupling, hydrofunctionalization, or hydrogenation reactions. Herein we report the synthesis and application of a novel class of phosphines bearing ylide substituents. These phosphines
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
Articles
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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