keYPhos^™

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.

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)

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.

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Yphos is a trademark of Umicore AG & Co. KG