Bulletin of the Korean Chemical Society

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Catalytic Enantioselective Fluorination Reactions of α-Cyano Acetates and α-Cyanophosphonates Using Chiral Palladium Complexes

  • Kim, Sun-Mi (Department of Chemistry, Soonchunhyang University) ;
  • Kang, Young-Ku (Department of Chemistry, Soonchunhyang University) ;
  • Cho, Min-Je (Department of Chemistry, Soonchunhyang University) ;
  • Mang, Joo-Yang (Department of Chemistry, Soonchunhyang University) ;
  • Kim, Dae-Young (Department of Chemistry, Soonchunhyang University)
  • Published : 2007.12.20
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Abstract

The catalytic enantioselective electrophilic fluorinations of active methane compounds promoted chiral palladium complexes have been developed. Treatment of α-cyano acetates and α-cyanoalkylphosphonates with N-fluorobenzenesulfonimide as the fluorine source under mild reaction conditions afforded the corresponding α-cyano-α-fluorinated adducts in high yields with excellent enantiomeric excesses (up to 99% ee). These reactions can be conducted in alcoholic solvents without any precaution to exclude water and moisture.

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