trans-[1,3-Bis(2,6-Di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) Dichloride (Pd-PEPPSITM-IPent)

[1158652-41-5] C40H56Cl3N3Pd (MW 791.67) InChI = InChI=1S/C35H53N2.C5H4ClN.2ClH.Pd/c1-9-26(10-2)30-19-17-20-31(27(11-3)12-4)34(30)36-23-24-37(25-36)35-32(28(13-5)14-6)21-18-22-33(35)29(15-7)16-8;6-5-2-1-3-7-4-5;;;/h17-29H,9-16H2,1-8H3;1-4H;2*1H;/q;;;;+2/p-2 InChIKey = MSZBXTMQAMAAOX-UHFFFAOYSA-L (precatalyst for Pd-mediated C–C, C–N, and C–S cross-coupling reactions)2-14 Physical Data: mp 195–201 °C. Solubility: soluble in most organic solvents except for aliphatic hydrocarbons (e.g., pentane or hexanes); insoluble in water. Form Supplied in: pale to dark yellow solid. Available from Sigma-Aldrich. Analysis of Reagent Purity: NMR analysis. Preparative Methods: heating PdCl2 (1.05 mmol), N,N-(2,6-di-pentylphenyl)imidazolium chloride (1; IPent·HCl; 1.0 mmol), and powdered Cs2CO3 (5.0 mmol) at 90 °C in neat 3-chloropyridine (5 mL) with vigorous stirring for 18 h (eq 1) afforded Pd-PEPPSITM-IPent (2; 80%) as a beige powder following filtration through a plug of silica gel/celite (CH2Cl2), vacuum distillation of excess 3-chloropyridine, a second filtration through a silica gel/celite plug, and trituration with pentane. Purification: precipitation with pentane from concentrated ether or CH2Cl2 solution or flash chromatography on silica gel (pentane : CH2Cl2 = 1:2). Handling, Storage, and Precautions: stable under ambient conditions in solid form or in solution. Incompatible with strong acids, bases, oxidizing, and reducing agents.