Synthesis of gem-Difluoroalkenes

  • Author: Angewandte Chemie International Edition
  • Published Date: 04 November 2017
  • Source / Publisher: Angewandte Chemie International Edition/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Synthesis of <i>gem</i>-Difluoroalkenes

Gary A. Molander and colleagues, University of Pennsylvania, Philadelphia, USA, have developed a method for the synthesis of gem-difluoroalkenes. These fluorinated compounds could serve as ketone mimics in pharmaceutical agents. Ketones themselves are uncommon because of their propensity to undergo reduction by aldo-keto reductases.

The team used a photoredox-promoted radical/polar crossover reaction, which provides a convergent route to the 1,1-difluoroalkene motifs under mild conditions. Primary, secondary, and tertiary radicals bearing a wide range of functional groups are produced in photocatalytic reactions. These radicals can readily add to trifluoromethyl-substituted alkenes to provide the corresponding gem-difluoroalkenes (example pictured) in high yield.

The researchers have also developed a synthesis of a bench-top-stable organotrifluoroborate reagent for the facile synthesis of trifluoromethyl-substituted alkenes from aryl bromides. According to the team, this approach could enable medicinal chemists to efficiently synthesize a library of these biologically relevant molecules.


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