Toluene → 2,2'-Dimethylbiphenyl

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This is an example of Pd/ligand 4-catalyzed aryl amination reaction for aryl amine synthesis. A reaction tube containing NaOtBu (120 mg, 1.25 mmol) was thoroughly evacuated and purged with argon. 5-Chloro-m-xylene (0.14 mL, 1.04 mmol), heptylmethylamine (0.21 mL, 1.25 mmol), a toluene solution of Pd(dba)2 (1.2 mL, 1.0 mg/mL, 2.1 μmol) and a toluene solution of ligand 4 (2.5 mL, 1.0 mg/mL, 6.2 ,μmol) and toluene (0.3 mL) were added to the reaction tube and the reaction was heated at 105° C. for 21.5 h. The reaction was taken up in ether (100 mL) and washed with H2O (30 mL) and brine (30 mL). The organic phase was dried over MgSO4, filtered and concentrated under vacuum. The crude product was purified by column chromatography on silica gel using hexanes/ethyl acetate as eluant to afford compound 2 (shown below in Table 1) as a yellowish oil (239 mg, 98%) after drying under vacuum. 1 H NMR (CDCl3): δ6.33 (br, 3H, ArH), 3.25 (t, J=7.6, 2H, —NCH2—), 2.89 (s, 3H, —N—CH3), 2.27 (s, 6H, Ar(CH3)2), 1.54 (br, 2H, —NCH2CH2—), 1.30 (br, 8H, —(CH2)4CH3), 0.89 (br t, J=6.6, 3 H, —CH3).

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