4.5 Article

Umpolung Reactivity of Fluoroalkylselenotoluenesulfonates: Towards a Versatile Reagent

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 8, Issue 5, Pages 675-678

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201900027

Keywords

trifluoromethylselenolation; nucleophilic substitution; trifluoromethylselenotoluenesulfonate; fluorine; synthetic methods

Funding

  1. Region Rhone Alpes
  2. Erasmus+ programme of the European Union
  3. Centre National de la Recherche Scientifique (CNRS)
  4. CPE Lyon
  5. French Fluorine Network
  6. French Ministry of Research

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Fluoroalkylselenotoluenesulfonates, which have already been described as selenolating reagents in electrophilic and radical reactions, can also be reduced by an organic electron donor (namely tetrakis(dimethylamino) ethylene or TDAE) to generate the corresponding fluoroalkylselenolate anions. Thus, the in-situ-formed anions react with various alkyl halides in a metal-free nucleophilic substitution. Trifluoromethyl- and higher perfluroalkylselenolated compounds have been obtained in modest to good yields.

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