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Generation and Reactions of Trifluoroacetimidoyl Radicals

1995; Oxford University Press; Volume: 68; Issue: 5 Linguagem: Inglês

10.1246/bcsj.68.1497

1348-0634

Yasufumi Dan‐oh, Hirokazu Matta, Junko Uemura, Hisayuki Watanabe, Kenji Uneyama,

Catalytic C–H Functionalization Methods

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.