[FeIII(F20-tpp)Cl] Is an effective catalyst for nitrene transfer reactions and animation of saturated hydrocarbons with sulfonyl and aryl azides as nitrogen source under thermal and microwave-assisted conditions

Abstract

[FeIII(F20-tpp)Cl] (F20tpp = meso- tetrakis(pentafluorophenyl)porphyrinato dianion) is an effective catalyst for imido/nitrene insertion reactions using sulfonyl and aryl azides as nitrogen source. Under thermal conditions, aziridination of aryl and alkyl alkenes (16 examples, 60-95% yields), sulfimidation of sulfides (11 examples, 76-96% yields), allylic amidation/amination of α-methylstyrenes (15 examples, 68-83% yields), and amination of saturated C-H bonds including that of cycloalkanes and adamantane (eight examples, 64-80% yields) can be accomplished by using 2 mol % [FeIII(F20- tpp)Cl] as catalyst. Under microwave irradiation conditions, the reaction time of aziridination (four examples), allylic amination (five examples), sulfimidation (two examples), and amination of saturated C-H bonds (three examples) can be reduced by up to 16fold (24-48 versus 1.5-6 h) without significantly affecting the product yield and substrate conversion. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA. Weinheim.