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.


Article Views: 2746

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from, please contact us first for permission and consult our permission guidance prior to making your request

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH