[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

Chemistry. 2010 Sep 10;16(34):10494-501. doi: 10.1002/chem.201000581.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Azides / chemistry*
  • Catalysis
  • Hydrocarbons / chemistry*
  • Hydrogen Bonding
  • Imines / chemistry*
  • Metalloporphyrins / chemistry*
  • Microwaves
  • Models, Molecular
  • Molecular Structure
  • Nitrogen / chemistry*
  • Sulfhydryl Compounds / chemistry*

Substances

  • Azides
  • Hydrocarbons
  • Imines
  • Metalloporphyrins
  • Sulfhydryl Compounds
  • phenylnitrene
  • Nitrogen