Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[C:9]1([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[C:3]1([CH3:8])[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1The above general procedure was followed using 2-bromotoluene (188 mg, 1.10 mmol) and diphenylamine (169 mg, 1.00 mmol) with 1 mol % Pd(dba)2 and 0.8 mol % tri-t-butylphosphine in 1.5 mL of toluene. After four hours, the reaction mixture was adsorbed onto silica gel and chromatographed with 2.5% ethyl acetate/hexanes to give 247 mg (95%) of N-(2-tolyl)diphenylamine as a colorless oil that crystallized to a white solid. 1H NMR (500 MHz, C6D6) δ 7.05-6.96 (m, 12 H), 6.78 (tt, J=7.25, 1.30 Hz, 2H), 1.99 (s, 3H). 13C NMR (125 MHz, C6D6) δ 148.0, 146.0, 136.6, 132.0, 129.9, 129.4, 127.7, 126.1, 122.0, 121.8, 18.7.
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