title: [Fe(III)(F(20)-tpp)Cl] is an effective catalyst for nitrene transfer reactions and amination of saturated hydrocarbons with sulfonyl and aryl azides as nitrogen source under thermal and microwave-assisted conditions.
abstract: [Fe(III)(F(20)-tpp)Cl] (F(20)-tpp=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 % [Fe(III)(F(20)-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 16-fold (24-48 versus 1.5-6 h) without significantly affecting the product yield and substrate conversion.
authors.affiliation: Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, China.
authors.forename: Yungen
authors.initials: Y
authors.lastname: Liu
authors.forename: Chi-Ming
authors.initials: CM
authors.lastname: Che
mesh_terms: D000586:Amination; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D006838:Hydrocarbons / Q000737:chemistry*; D006860:Hydrogen Bonding; D007097:Imines / Q000737:chemistry*; D008665:Metalloporphyrins / Q000737:chemistry*; D008872:Microwaves; D008958:Models, Molecular; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D001386:Azides; D006838:Hydrocarbons; D007097:Imines; D008665:Metalloporphyrins; D013438:Sulfhydryl Compounds; C017621:phenylnitrene; D009584:Nitrogen