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

J. Cassayre (1) , D. Dauge (1) , Samir Z. Zard (1, 2)

1 ICSN - Institut de Chimie des Substances Naturelles
2 DCSO - Laboratoire de synthèse organique

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.

J. Cassayre, D. Dauge, Samir Z. Zard. Influence of copper(II) acetate on Ni/AcOH-promoted 5-endo and 5-exo radical cyclisations of trichloroacetamides. SYNLETT, 2000, 4, pp.471-474. ⟨10.1055/s-2000-6556⟩. ⟨hal-00954902⟩