Influence of copper(II) acetate on Ni/AcOH-promoted 5-endo and 5-exo radical cyclisations of trichloroacetamides

Abstract : 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.
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Submitted on : Tuesday, March 11, 2014 - 1:34:23 PM
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J. Cassayre, D. Dauge, Samir Zard. Influence of copper(II) acetate on Ni/AcOH-promoted 5-endo and 5-exo radical cyclisations of trichloroacetamides. SYNLETT, Georg Thieme Verlag, 2000, pp.471-474. ⟨10.1055/s-2000-6556⟩. ⟨hal-00954902⟩

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