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Synlett 2000; 2000(4): 471-474
DOI: 10.1055/s-2000-6556
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Influence of Copper(II) Acetate on Ni/AcOH-promoted 5-endo and 5-exo Radical Cyclisations of Trichloroacetamides

Jérôme Cassayre* , Delphine Dauge, Samir Z. Zard
  • *Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-Sur-Yvette, France; Fax +33 (0) 1 69 33 30 10; E-mail: sam.zard@icsn.cnrs-gif.fr
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Publication Date:
31 December 2000 (online)

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Incorporation of Cu(OAc)2 as oxidant in Ni/AcOH-promoted 5-endo radical cyclisations of N-alkenyl-trichloroacetamides allows an interesting control of the oxidation level of the products, as illustrated by the conversion of 3 into either 4 or 5. In addition, allylic trichloroacetamides 13a-f under the same conditions underwent a 5-exo radical cyclisation-oxidation sequence leading to unsaturated hydroindolones, which represent valuable synthetic intermediates.

nickel - Cu(OAc)2 - trichloroacetamide - 5-endo radical cyclisation - 5-exo radical cyclisation