5-exo Cyclisation of vinyl-, aryl- and alkyl-radicals onto the aryl group of arylcarboxamides is followed by beta-scission of the resulting spirocyclohexadienyl radicals with ejection of a carbamoyl radical. The fate of this radical depends on the substrate but, in the cases studied, either 5-endo cyclisation or direct reduction follows to give phthalimides, biaryls or beta-arylethylamines.
Robertson, J., Palframan, M. J., Shea, S. A., Tchabanenko, K., Unsworth, W. R., & Winters, C. (2008). Radical 1,4-aryl transfer in arylcarboxamides leading to phthalimides, biaryls and enantiomerically enriched beta-arylethylamines. Tetrahedron, 64(52), 11896-11907. https://doi.org/10.1016/j.tet.2008.07.118