Hydroamination of ethylene by aniline: catalysis in water

Pavel Dub (1, 2) , Mireia Rodriguez-Zubiri (3) , Christine Baudequin (4) , Rinaldo Poli (1, 5)

1 LCC - Laboratoire de chimie de coordination
2 INEOS - A. N. Nesmeyanov Institute of Organoelement Compounds
3 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation
4 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
5 IUF - Institut universitaire de France

The platinum-catalyzed and halide-promoted hydroamination of ethylene with aniline is reported for the first time in the presence of simple sodium halides in water. Compounds K2PtX4 (X = Cl or Br), PtX2 or PtX4 (0.3% mol) in the presence of an aqueous solution of excess NaX and aniline under ethylene pressure (25 bar) affords N-ethylaniline with 60–85 turnovers after 10 h at 150 °C. The best result (TON = 85) was obtained in the presence of excess NaBr, whereas a slightly lower activity was observed with NaCl (60 cycles) and practically no activity with NaF or NaI (2–4 cycles). The reaction also produces N,N-diethylaniline (up to 1 cycle) and 2-methylquinoline (up to 8 cycles) as by-products. The influence of added H+ and different oxidizing agents was also examined.

Mots clés: platinum; hydroamination of ethylene; aniline; catalysis in water

Domaines: Catalyse; Chimie organique

Pavel Dub, Mireia Rodriguez-Zubiri, Christine Baudequin, Rinaldo Poli. Hydroamination of ethylene by aniline: catalysis in water. Green Chemistry, 2010, 12 (8), pp.1392-1396. ⟨10.1039/C004727A⟩. ⟨hal-02385300⟩