We herein report a new catalytic method for intermolecular olefin aminofluorination using earth-abundant iron catalysts and nucleophilic fluoride ion. This method tolerates a broad range of unfunctionalized olefins, especially nonstyrenyl olefins that are incompatible with existing olefin aminofluorination methods. This new iron-catalyzed process directly converts readily available olefins to internal vicinal fluoro carbamates with high regioselectivity (N vs F), many of which are difficult to prepare using known methods. Preliminary mechanistic studies demonstrate that it is possible to exert asymmetric induction using chiral iron catalysts and that both an iron-nitrenoid and carbocation species may be reactive intermediates.
We herein report a new catalytic method for intermolecular olefin aminofluorination un class="Chemical">sing earth-abundant iron catalysts and nucleophilic fluoride ion. This method tolerates a broad range of unfunctionalized olefins, especially nonstyrenyl olefins that are incompatible with existing olefin aminofluorination methods. This new iron-catalyzed process directly converts readily available olefins to internal vicinal fluoro carbamates with high regioselectivity (N vs F), many of which are difficult to prepare using known methods. Preliminary mechanistic studies demonstrate that it is possible to exert asymmetric induction using chiral iron catalysts and that both an iron-nitrenoid and carbocation species may be reactive intermediates.
Authors: Qi Zhang; David P Stockdale; Jason C Mixdorf; Joseph J Topczewski; Hien M Nguyen Journal: J Am Chem Soc Date: 2015-09-10 Impact factor: 15.419
Authors: Sayanti Chatterjee; Ingolf Harden; Giovanni Bistoni; Rebeca G Castillo; Sonia Chabbra; Maurice van Gastel; Alexander Schnegg; Eckhard Bill; James A Birrell; Bill Morandi; Frank Neese; Serena DeBeer Journal: J Am Chem Soc Date: 2022-02-04 Impact factor: 15.419