Metal-Free Catalytic Asymmetric Fluorination of Keto Esters Using a Combination of Hydrogen Fluoride (HF) and Oxidant: Experiment and Computation

Roman Pluta, Patricia E. Krach, Luigi Cavallo, Laura Falivene*, Magnus Rueping

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

57 Scopus citations

Abstract

A chiral iodoarene organocatalyst for the catalytic asymmetric fluorination has been developed. The catalyst was used in the asymmetric fluorination of carbonyl compounds, providing the products with a quaternary stereocenter with high enantioselectivities. Chiral hypervalent iodine difluoride intermediates were generated in situ by treatment of the catalyst with an oxidant and hydrogen fluoride as fluoride source. As such, the α-fluorination of a carbonyl compound was achieved with a nucleophilic fluorine source. A combined computational and experimental approach provided insight into the reaction mechanism and the origin of enantioselectivity.

Original languageEnglish (US)
Pages (from-to)2582-2588
Number of pages7
JournalACS Catalysis
Volume8
Issue number3
DOIs
StatePublished - Mar 2 2018

Bibliographical note

Publisher Copyright:
© 2018 American Chemical Society.

Keywords

  • DFT study
  • fluorine
  • hypervalent compounds
  • reaction mechanism
  • transition state

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

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