Generation and Reactions of Trifluoroacetimidoyl Radicals

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Abstract
N-Aryltrifluoroacetimidoyl radicals have been generated by three different methods: the tin-radical promoted deiodination and photochemical homolysis of imidoyl iodides and the thermal homolysis of imidoyl azo-compounds. N-[2-(1-alkynyl)phenyl]trifluoroacetimidoyl iodides have been converted to trifluoromethylated indoles by the tin-radical promoted homolysis of the carbon–iodine bond followed by intramolecular cyclization. The photolysis of trifluoroacetimidoyl iodides enabled both intra- and intermolecular cyclization to indoles and quinolines. Likewise, thermal reactions of N-(2,2,2-trifluoro-1-tritylazoethylidene)anilines provided trifluoromethylated quinolines and indoles.