N,N′-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene palladium(I) Allyl Chloride

[478980-04-0] C24H29ClN2Pd (MW 487.37) InChI = 1S/C21H24N2.C3H5.ClH.Pd/c1-14-9-16(3)20(17(4)10-14)22-7-8-23(13-22)21-18(5)11-15(2)12-19(21)6;1-3-2;;/h7-12H,1-6H3;3H,1-2H2;1H;/q;;;+1/p-1 InChIKey = PBWADPFFHMNMFI-UHFFFAOYSA-M (used for cross-coupling reactions, aryl amination, cyclization–trapping of bisdiene, polymerization of olefins, allylation of alkylidenes malonitriles, oxidation of secondary alcohols) Data: mp >165 °C. Solubility: acetone, CH2Cl2, partially soluble in toluene and DMSO, insoluble in water, pentane, hexane, and diethyl ether. Form Supplied in: white solid, crystal structure available.1 Preparative Methods: [Pd(IMes)(allyl)Cl] is easily obtained by reaction in a Schlenk tube of 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene with [Pd(allyl)Cl]2 in dry THF at room temperature for 1 h. Solvent is removed under reduced pressure and the product triturated with hexane and then filtered under air to provide the complex as a solid in high yield.2 Purification: crystallization from THF/hexanes solution.1 Handling, Storage, and Precautions: described as air and moisture stable. Nevertheless, the complex should be stored under an inert atmosphere.