N,N,N',N'-Tetramethylethylenediamine

Typical procedue: A 50 mL flask is placed in a water bath at rt, charged with magnesium turnings (58 mg), fitted with a rubber septum, and purged with argon. A solution of FeCl3 (16.2 mg) in dry THF (8 mL) is added via syringe followed by TMEDA (362 micro-L). The mixture is stirred at rt for 20 min. Then, the reaction is cooled to 0°C, and 4-bromotoluene (342 mg) and bromocyclohexane (391 mg) are added. After 3 h at 0°C, the reaction is quenched with saturated aqueous NH4Cl (5 mL) and aqueous HCl (10%, 2 mL) and extracted with ethyl acetate (3 x 10 mL). The combined organic phases are dried over Na2SO4, concentrated in vacuo, and purified by silica gel flash chromatography (cyclohexane / ethyl acetate) to give 244 mg of 1-cyclohexyl-4-methylbenzene in 70% yield.