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Synlett 1991; 1991(4): 231-232
DOI: 10.1055/s-1991-20688
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A Facile Synthesis of 2-Amino-2′-hydroxy-1,1′-binaphthyl and 2,2′-Diamino-1,1′-binaphthyl by Oxidative Coupling Using Copper(II) Chloride

Martin Smrčina* , Miroslav Lorenc, Vladimír Hanuš, Pavel Kočovský
  • *The J. Heyrovský Institute of Physical Chemistry and Electrochemistry ČSAV, CS-182 23 Prague 8, Czechoslovakia
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Publication Date:
07 March 2002 (online)

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Oxidative coupling of a 1:1 mixture of 2-naphthol (1) and 2-naphthylamine (2) by means of copper(II) chloride in the presence of benzylamine gives the cross-coupled product 3 (2-amino-2′-hydroxy-1,1′-binaphthyl) in 68% yield while copper(II) chloride itself yields mainly the homo-coupled diamine 4 (2,2′-diamino-1,1′-binaphthyl) in 33% yield. Pure 4 was prepared by oxidation of 2-naphthylamine (2) using (PhCH2NH2)4CUCl2 in 58% yield.

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