913030
trYPhos™
Umicore
Synonyma:
(CyYPhos)(Me)PtBu2, Tricyclohexyl(1-(di-tert-butylphosphanyl)ethylidene)phosphane
Přihlásitk zobrazení cen stanovených pro organizaci a smluvních cen
About This Item
Empirický vzorec (Hillův zápis):
C28H54P2
Číslo CAS:
Molekulová hmotnost:
452.68
MDL number:
UNSPSC Code:
12352001
NACRES:
NA.22
Doporučené produkty
Quality Level
form
powder
reaction suitability
reagent type: ligand
mp
137-139 °C
functional group
phosphine
SMILES string
[P](=C(P(C(C)(C)C)C(C)(C)C)C)(C3CCCCC3)(C2CCCCC2)C1CCCCC1
InChI
1S/C28H54P2/c1-23(29(27(2,3)4)28(5,6)7)30(24-17-11-8-12-18-24,25-19-13-9-14-20-25)26-21-15-10-16-22-26/h24-26H,8-22H2,1-7H3
InChI key
TYHSTNKVOIFVOF-UHFFFAOYSA-N
General description
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.
Application
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)
Features and Benefits
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.
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
related product
Č. produktu
Popis
Stanovení ceny
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Vyberte jednu z posledních verzí:
Osvědčení o analýze (COA)
Lot/Batch Number
Je nám líto, ale pro tento produkt momentálně nemáme COA k dispozici online.
Potřebujete-li pomoc, obraťte se na Zákaznická podpora
Již tento produkt vlastníte?
Dokumenty související s produkty, které jste v minulosti zakoupili, byly za účelem usnadnění shromážděny ve vaší Knihovně dokumentů.
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
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
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
Sortimentní položky
Explore innovative palladium-catalyzed coupling reactions with ylide-substituted phosphines. Learn about their impressive capabilities, enabling milder conditions and access to aryl chlorides.
YPhos ligands enable efficient palladium-catalyzed coupling reactions under mild conditions, enhancing the synthesis of complex organic molecules.
Náš tým vědeckých pracovníků má zkušenosti ve všech oblastech výzkumu, včetně přírodních věd, materiálových věd, chemické syntézy, chromatografie, analytiky a mnoha dalších..
Obraťte se na technický servis.