Aniline → Diphenylamine

Participants

Reaction Steps

The general procedure from Example 1 was followed using chlorobenzene (135 mg, 1.2 mmol) and aniline (93 mg, 1.0 mmol) with Pd2(dba)3 (25 mg, 0.027 mmol) and (Me3C)2PH(O) (7.0 mg, 0.042 mmol) and NaOtBu (144 mg, 1.5 mmol) in 2.0 mL of toluene. After 24 h, the reaction mixture was chromatographed with 5% ethyl acetate/hexane to give 51 mg (30% yield) of diphenylamine. It was >95% pure by 1H NMR and GC/MS. 1H NMR (500 MHz, CDCl3): δ 7.18 (m, 4H), 6.99 (d, J=7.68 Hz, 4H), 6.84 (t, J=7.34 Hz, 2H), 5.59 (br, 1H) ppm. 13C NMR (125 MHz, CDCl3): d 143.1, 129.3, 120.9, 117.8 ppm. MS: Calculated for C12H11N(M+): 169.1. Found: 170.3 (M++H).

Provenance & Evidence