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Issue 8, 2010
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Hydroamination of ethylene by aniline: catalysis in water

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Abstract

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.

Graphical abstract: Hydroamination of ethylene by aniline: catalysis in water

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Publication details

The article was received on 29 Mar 2010, accepted on 27 May 2010, published on 23 Jun 2010 and first published online on 23 Jun 2010


Article type: Paper
DOI: 10.1039/C004727A
Citation: Green Chem., 2010,12, 1392-1396
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    Hydroamination of ethylene by aniline: catalysis in water

    P. A. Dub, M. Rodriguez-Zubiri, C. Baudequin and R. Poli, Green Chem., 2010, 12, 1392
    DOI: 10.1039/C004727A

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