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质量水平
表单
powder
反应适用性
reagent type: ligand
mp
137-139 °C
官能团
phosphine
SMILES字符串
[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
一般描述
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.
应用
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)
特点和优势
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.
法律信息
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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储存分类代码
11 - Combustible Solids
WGK
WGK 3
闪点(°F)
Not applicable
闪点(°C)
Not applicable
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
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), 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
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
商品
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.
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