913294

keYPhos^™

Umicore

• Synonym(s): CyYPhos(Me)PCy₂, Tricyclohexyl(1-(dicyclohexyl-phosphanyl)ethylidene)-phosphane
• Empirical Formula (Hill Notation): C₃₂H₅₈P₂
• CAS Number: 14185-94-5
• Molecular Weight: 504.75
• UNSPSC Code: 12352001
• NACRES: NA.22

Properties

• product name: keYPhos^™,
• form: powder
• Quality Level: 100
• reaction suitability: reagent type: ligand
• mp: 167-169 °C
• functional group: phosphine

Description

General description

keYPhos^™is an ylide-functionalized phosphine ligand developed in the lab of Prof. V. Gessner at the Ruhr-University Bochum with demonstrated uses in Pd-catalyzed cross coupling reactions, including the arylation of ketones and arylation of amines. keYPhos^™ is part of the YPhos^™ family of ligands, also containing the joYPhos^™ and trYPhos^™ ligands.

Application

The electron-rich and sterically demanding keYPhos^™ has a methyl group in the ylide-backbone and is a valuable ligand for the palladium catalyzed coupling of aryl chlorides with primary and secondary alkyl and aryl amines at room temperature. keYPhos^™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.

Learn more about ylide-functionalized phosphines (YPhos)

Features and Benefits

Advantages of the keYPhos^™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. keYPhos^™ has been shown to perform well with common palladium sources such as Pd₂(dba)₃, Pd(OAc)₂, [Pd(allyl)Cl]₂ or [Pd(cinamyl)Cl]₂.

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.

Yphos is a trademark of Umicore AG & Co. KG

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable