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J Am Chem Soc. 2016 Sep 7;138(35):11360-7. doi: 10.1021/jacs.6b07221. Epub 2016 Aug 26.

Iron(II)-Catalyzed Intermolecular Aminofluorination of Unfunctionalized Olefins Using Fluoride Ion.

Author information

1
Department of Chemistry, Georgia State University , 100 Piedmont Avenue SE, Atlanta, Georgia 30303, United States.

Abstract

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.

PMID:
27529196
PMCID:
PMC5050046
DOI:
10.1021/jacs.6b07221
[Indexed for MEDLINE]
Free PMC Article

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