A tandem carbonylation/cyclization radical process of 1-(2-iodoethyl)indoles and pyrrole

Article abstract of DOI:10.1016/S0040-4039(99)01346-5

The AIBN-induced radical reaction of 1-(2-iodoethyl)indoles and pyrroles with Bu₃SnH under 80 atm of CO was examined. Carbon monoxide was efficiently trapped by an alkyl radical to form an acyl radical which underwent intramolecular addition to the aromatic system to produce bicyclic aromatic ketones after in situ oxidation.