General procedure for the synthesis of bis(2,6-dimethylbenzene)amine from 2,6-dimethylbromobenzene and 2,6-dimethylaniline: in a Schlenk tube equipped with a magnetic stirrer, base (3.0 mmol), PdCl2(Ph3P)2 (3.5 mg, 0.5 mol%), Ph3P (2.6 mg, 1.0 mol%), 2,6- dimethylaniline (1.0 mmol) and 2,6-dimethylbromobenzene (2.5 mmol) in o-xylene (8.0 mL) solution. The reaction mixture was heated to reflux and stirred for 8 hours (or 12 hours) under nitrogen protection. Upon completion of the reaction, the solvent was evaporated under reduced pressure and the residue was purified by fast column chromatography (eluent: petroleum ether/ethyl acetate) to afford the target product, bis(2,6-dimethylphenyl)amine.
